


The Gang Leader's Love

by Wayward_Sinner



Category: Supernatural
Genre: Alternate Universe, Angst, Angst with a Happy Ending, Bottom Castiel, Bottom Dean, Fluff, Fluff and Smut, Happy Ending, It's all legal, Jealous Castiel, M/M, Mostly POV Dean, Past loving in highschool, Smut, Some POV Cas, Top Castiel, Top Dean, everything else isn't really, slow-burn, they're 18, well the sex is
Language: English
Status: Completed
Published: 2018-04-11
Updated: 2018-11-29
Packaged: 2019-04-21 16:50:12
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 11
Words: 23,059
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14289195
Author URL: https://archiveofourown.org/users/Wayward_Sinner/pseuds/Wayward_Sinner
Summary: Based off a prompt from writing.prompt.s:During a bank robbery, the criminals recognize you and retreat. Later you discover they work for your high school sweetheart who is now a major crime boss. To make matters more interesting, he's put you on a "No Harm" list. Maybe it's time to pay him a visit. (Paraphrasing the prompt)





	1. The Night it all went to Shit

**Author's Note:**

> I don't have a beta (I think that's what they're called) so all the mistakes are mine. If you see any, let me know and I can change them. Enjoy!!!

“This is crazy!” Dean called, his voice full of panic as he was led into the abandoned building.

  
“Live a little,” Cas said with a laugh, ignoring Dean’s panic.

  
They entered the old building, the only light came from the shattered windows. The cement floor was covered in dust, screws, garbage, and liquid of some kind. Dean carefully steered away from the pool, nervous to discover what it was.

  
“Oi! Angel boy.”

  
Dean and Cas both stopped as a familiar voice spoke. “Crowley!” Cas said smoothly and walked towards the young man. He was sitting on an old couch that had springs popping free.

  
“Did you manage to get what I wanted?”

  
“I did,” Cas said proudly.

  
Crowley’s thin lips curled into a smile. “Good lad.” He turned over his shoulder ever so slightly to speak to the men who were standing guard along the wall. “Get it.”

  
Two men came forward and took the backpack Cas had brought. “And my money?”

  
Crowley just laughed. “About that…”

  
Everything happened so quickly. One moment, Dean and Cas were standing across from Crowley and his men, and in the next, everyone was running. Crowley disappeared through a back door just as a group of police officers burst through the door. “Police! Everyone down!”

  
“Dean go.” Cas said quickly. They had been standing next to a tall column and had yet to be seen.

  
“What? No. Come with me.” Dean argued.

  
“Crowley must have told them about me. He didn’t know you’d come. Go!” Cas pushed him away and then ran out into the open.

  
Dean wanted to run after him but images of little Sammy came flooding into his mind. Cas was tough. He’d be okay. Sammy still needed him.  
And with that, they parted ways.


	2. The Robbery

**Summary for the Chapter:**

> Dean gets into some trouble.

14 years later

 

Dean Winchester sat in his office, staring at the grey walls. Winchester Trades is his father’s business. He had started it with his best-friend Bobby Singer and it quickly became one of the biggest trading companies in all of New York. John Winchester had hired his son, Dean after he completed his bachelors in business. Sam, the younger of the two brothers, had been offered a position as well but declined to start his own law firm with his college roommate Garth.

Though their lives were busy, boring or somehow a combination of the two, it wasn’t half bad. Dean was going to take over the business once his father and Bobby retired, Sam was already a top-notch lawyer here in the city… yeah, life was not bad.

“Hey, Dean?” Charlie, his secretary, and best friend called, poking her head into his office. “The Bank Manager called and said that there was an issue with the cheque you sent yesterday.”

“Patch her through,” Dean said and reached for the desk phone.

“She asked if you could go down.”

Dean groaned then nodded his head. “Fine.” He rose from his glass desk and grabbed his jacket from Charlie. “Thank you.”

“Maybe some fresh air will do you good. You’re too young to be so stressed.” Charlie said softly.

“Maybe…” Dean said slowly. He offered Charlie a smile and then he made his way to the bank.

 

The bank was just a block away from their office. The building was old-fashioned as it was made out of marble and mahogany. Inside was marble flooring that reflected the light from the grand chandelier.

Dean unbuttoned his coat and went to the bank teller. “Dean Winchester to see the manager.”

“Yes. One moment Mr. Winchester.” The teller came back to lead Dean to the back office.

“Ah, Mr. Winchester, I just needed your signature here.”

Dean stifled a groan. Yeah, he had to come down to do that, but it was such a stupid tedious thing. He picked up the pen and scribbled his name on the cheque where he had forgotten it.

He stood up to leave but stopped as he heard shouting and screaming. The manager rushed to the door and gasped. Dean followed her and froze as he saw at least twelve men, all dressed in black suits and all wearing blank white masks that had slits for the eyes.

Each of them had a large gun and many were aiming them at the people at the bank. Dean knew better than to try and fight, there were just too many. Instead, he dropped to his knees like everyone else and held his hands behind his head. He watched as three of men stayed with the hostages and the others disappeared around a corner to where the safe was kept.

He expected to hear drilling, but he just heard the gears turning and the sound of air being released as it opened. They had the code somehow…

Ten minutes had passed and it seemed like they were almost done emptying the safe.

“Why aren’t the police here yet?” A hostage said.

The girl had a point. For something like this, the police should have been here within the first two minutes or so.

“Shut your mouth.” One of the men said. He got close to the girl who had spoken and pressed the end of the barrel of his gun to her forehead.

“Hey!” Dean called. “C’mon man. Just take what you want. There’s nothing we can do so just leave us.”

The man turned to Dean, and even with the mask, Dean could tell he was surprised. He took a step back then ran to the other two. He spoke to them and then they stared at Dean in shock as well. The first man disappeared around the corner and many of the men who were emptying the safe peered around the corner.

Dean’s brows knit together in confusion.

“We should go.” The first man said.

All the men came forward. “We’re not done.”

“If the police get here, it could get messy. We can’t risk… you know…” He said slowly and jerked his chin towards Dean.

“Fine.” They cursed then within seconds, they were gone with most of the safe’s contents. As soon as they were gone, the police burst through the doors. Dean answered their questions, but he didn’t tell them that he seemed to have caused them to leave. He didn’t know if that was what happened, but something didn’t seem right.

**Notes for the Chapter:**

> Future chapters will hopefully be a bit longer. Also, I will probably try to post a new chapter every Monday and Friday so expect another tomorrow. Hope you enjoyed!


	3. Twig and Berries

**Summary for the Chapter:**

> Dean discovers some secrets and truths.

            “Jesus Christ!” Sam cried as he ran into Dean’s office.

 

            Dean groaned as his brother joined the group. His father, honorary Uncle Bobby, Charlie and now Sam had been pestering him since he returned from the station. They had heard about the robbery through the radio and it was all over social media. Dean had called them as soon as he could to tell them he was fine, but he still had to stay at the station for just over an hour to make sure he had answered all their questions.

 

            This had been the second bank robbery in the last three months but so far there was no connection. Not that Dean really cared. He was tired and he had orders to fill out.

 

            “Son.” His father said sternly. “Take the rest of the week off. Yeah, you’re not bruised but that can be traumatizing.”

 

            “I have work to do.”

 

            “We can do it,” Charlie said, John and Bobby both nodded their heads in agreement

 

            Dean wanted to argue but he found himself agreeing with them. “Fine.”

 

            “I’ll drive you,” Sam said.

           

            “I have my car.”

 

            “I took a cab here. I ride my bike to work so I can drive Baby.”

           

            Dean did not seem impressed by the situation but he could feel his eyes grow heavy. “Let’s go.”

 

            They took the elevator down to the garage. “You sure you’re okay?”

 

            Dean was going to say that he’s _fine_ because that’s his usual response, but he really wanted to talk about what happened. “They left because of me.”

 

            Sam’s jaw tightened in confusion. “Did you fight them?”

           

            “No. They just saw me and decided to go.” Dean shook his head. “I know it sounds crazy. But you would have thought the same if you had seen the way they looked at me. They were so surprised and they were worried about something.”

 

            Sam was quiet as he got into the driver’s seat of the car and headed in the direction of Dean’s apartment.

 

            “Say something, Sammy.”

 

            “Dean… It’s far-fetched. You were probably just trying to make sense of all the crazy.”

 

            Dean rolled his eyes. “Don’t do that thing.”

 

            “What thing?”

 

            “Where you try to make sense of everything but you make it more about mind shit and mental health.”

 

            “I don’t do that!”

 

            “No? Okay well, let’s see. You blamed my break-up with Lisa on me subconsciously wishing she had a dick instead of just acknowledging that we didn’t work and fell out of love. But when I dated Benny for a bit, you blamed that break-up on my stress levels at work, when we actually just broke up because we were better friends. Oh!” Dean said quickly because Sam opened his mouth. “It’s not just relationships. When I joined a baseball league in college, you said it was to hide my bisexuality and cover for the gayness that seeps through. Even though I’ve always been open about it and I’m not exactly a stereotypical gay guy so, there hasn’t been anything to really _hide_.”

 

            “Dean—”

 

            “No Sam. Just admit that you make simple things into bullshit psychology experiments or whatever. Lisa, Benny and I broke up over normal things. I played baseball ’cause I like it. Those guys from the bank left because of me for some reason. Yeah, I still don’t get all of it, but there is no need to make it about subconscious things.”

 

            Sam was quiet for a few minutes after that. When he spoke, it was soft and full of regret. “I don’t mean to dismiss your feelings or make things worse by adding the ideas of subconscious behavior. What I did with your relationships and with baseball wasn’t right and I know that it bothers you, and I’m sorry for that. I do read into things too much. But I really think the likely hood of those thieves getting scared because of you is slim.”

 

            “I can agree with that,” Dean said throwing his hands in the air. “I know it’s unlikely, but it doesn’t change the fact that it happened.”

 

            “Okay,” Sam said in defeat. “Let’s say they left because of you—”

 

            “They did.”

 

            Sam ignored him. “Why would they? Yeah, you’re a well-known businessman and so anything that happens to you would be all over the news.”

 

            “Right.” Dean agreed and got out of the car as they parked in the underground garage of his building. They entered the elevator and after Dean punched in his code, they went up to his penthouse. “But that is a classy bank, you know what I mean? I saw a few others at the same level and I’m sure the guys robbing it would have known that.”

 

            Sam nodded his head. “That’s true. So what’s special about you?”

 

            “Hey! I’m awesome.”

 

            Sam rolled his eyes. “Yes, Dean. You’re so awesome. Look, you should rest. I’m going to call Garth for a ride. Goodnight Dean.”

           

            “It’s six.”

           

            “You should go to bed.” And then Sam left.

 

            Dean was tired as hell. But he couldn’t stop thinking about what had happened. He sat on his couch and turned the TV to the local news. Sure enough, they were talking about the robbery.

 

            Dean leaned back on the couch, beer in hand and watched them say basically the same things over and over again. They played a few clips of robbery but Dean was there so not much was new. At least that was until he saw the tattoo.

 

            One of the men that were filling the bags with gold bars had his sleeve pulled back ever so slightly and revealed a very familiar tattoo on his wrist. Golden wings, outlined in black with a thin silver and intricate sword running vertically through the middle of the wings. It was their family crest of sorts. All the brothers in that family wore them.

 

            “Gabriel…” Dean said softly in shock. But that couldn’t be right. Gabe had gone to culinary school and last Dean had heard of him, he had a cute little café in Manhattan. He was a rich man; why would he be stealing from a bank?

 

            Dean grabbed his phone. It read that it was past six, so Charlie would be home by now. He dialed her number.

 

            “Hey, bitch! How are you doing?”

 

            “Hey, Charlie… I need a favor.”

 

            “Yes, Sir.”

 

            “But I need Charlie the hacker, not Charlie my secretary,” Dean said nervously.

 

            There was silence on her end for a few moments. “Why?”

 

            “I need you to look up a Gabriel Novak.”

 

            He could hear her moving around her apartment and he heard her typing on her computer. “I have a few. Is he local?”

           

            “Yeah, he lives in Manhattan,” Dean said, twisting the paper off the bottle nervously.

 

            “Okay, I got him. What do you want to know?”

 

            “Has he come into a large sum of money lately?”

 

            “Hmm…”

 

            He could hear Charlie piecing together his own thoughts.

 

            “You think he was a part of the robbery?”

 

            “Maybe. I just need to know about his funds.”

 

            “Well, he makes a lot of money as it is. I’m not seeing any recent big deposits.”

 

            Dean was quiet for a moment. “Check around three months ago.” That was the other robbery and the police were suspecting it had been the same gang.

 

            “I’m not… Oh, wait. There’s an additional couple thousand here and there. It wouldn’t have been that noticeable had they not been so spread out.” Charlie then chose her next words carefully. “Dean, you should report this to the police if you think this is one of the guys.”

 

            “No!” He found himself saying quickly. “I just need to check something first.”

 

            “Tell me you’re not going to go see this guy, Dean.”

 

            “Charlie I’ve got to go.” Dean hung up before she could try and talk him out of it. He looked up Gabriel’s café, Twig and Berries (well at least he still had his charming humor). It was open late and the chances of Gabriel being there after the robbery were slim, but Dean had to take the chance.

 

            He grabbed his coat and raced down to the garage. He punched in the address and drove for over twenty minutes. The building was square and took up a corner on the main street. It was made of red brick and had a beautiful flower full patio out front that wrapped around the side of the building. Dean parked the car in the, thankfully, nearly empty lot, and entered through the stained glass doors.

 

            He had driven past the café many times but had never stepped inside. Despite the name of the place, it was very classy inside. Most of the tables were low and had comfy circular chairs. The lighting was dim and calm. There weren’t many people there despite it being a popular time for restaurants. There was one girl behind the counter cutting up fruits and vegetables. She looked up as Dean entered and smiled.

           

            “Hello, how can I help you?”

 

            “Is Gabriel here?”

 

            To his surprise, she nodded. “He’s in the back office. I’ll go get him.”

 

            Dean stood at the bar, waiting patiently. He knew he was about to see Gabriel, the elder brother to his first love, but his heart still dropped when he saw him.

 

            The short man walked out of the office, speaking before seeing Dean. “Whatever it is, I didn’t do it.” When he laid eyes on Dean, he froze.

 

            “Funny,” Dean said dryly, shoving his hands in his pockets. “But are you sure about that?”

 

            “Well, fuck.” Gabriel cursed, running a hand through his golden locks. “Dean… It’s been a long time.”

 

            “Yeah.”

 

            “How you been?” Gabriel asked, his stance was tall and proud, but his voice shook with nervousness.

 

            Dean wasn’t interested in small talk. “I know what happened, Gabe. Just be honest with me.”

 

            “I don’t know what you’re talking about.” Gabe said, leaning on the counter towards Dean.

 

            “Bullshit.”

 

            Gabe’s lips curled in thought. He turned to his employee and said, “I’m just going to have a chat with him. I’ll hop on if it gets busy.”

 

            The girl nodded her head, clearly not sensing the tension.

 

            Gabe walked around the counter and led Dean to a booth by the long windows. They sat across from each other, glaring. “Elephant in the room. You know I was one of the guys to…”

 

            “Rob a bank.”

 

            Gabe chuckled. “Are you wearing a wire?”

 

            “I haven’t spoken to the police.”

 

            “Why not?” Gabe’s eyes were glowing with curiosity.

 

            “Because I want to know what happened. You all left before you planned. Why?”

 

            “Because of you, gorgeous.”

 

            _I knew it_. “But _why_?”

 

            Gabe cursed. “Because little Castiel has made quite the name for himself and now runs a global crime syndicate. After your separation, he was worried about what would happen to you. Once he had enough power, he put your name on a _no harm_ list.”

 

            “Why would he do that?”

 

            “Why don’t you ask him yourself. He just walked in.”

**Notes for the Chapter:**

> Ooo... Cliffhanger!  
> And yeah, Sam is a little crazy but you'll find out why, at some point.  
> Also a new chapter on Monday


	4. Confessions

**Summary for the Chapter:**

> Cas reveals his past.

**Notes for the Chapter:**

> So this chapter is a lot longer but I hope you enjoy it!

 

           Dean’s whole body tensed. His palms grew sweaty and his eyes were going in and out of focus. Very slowly, he looked over his shoulder. There in all his glory, stood Castiel.

 

            His hair was beautifully dark and untamed. He was just a bit taller and leaner then he had been when they were eighteen. He was wearing a black suit under—sweet fuck—he still had the dirty old trench coat. His cheeks were more defined and though he looked older, he was far from looking old. He had matured nicely like a fine French wine. And when vibrant hypnotizing blue eyes met green, the world stopped.

 

            Memories of their past surged before them.

 

            _Dean had been walking to recess, now that lunch was over. The second grade was harder than he thought it was going to be, but he was doing okay. He left the school and went to the playground. That was where he saw Castiel for the first time. He was the new kid which explained why Azazel and his gang were currently beating him up._

_Dean had witnessed many fights but he had never interfered. He had always been outnumbered. But as soon as he saw Castiel’s face, his heart sank. Out of nowhere, a rush of adrenaline coursed through his veins. In the next moment, he was running to Azazel and pushing him to the ground. He pushed Ruby back, not caring about the fact that she was a girl. And then he pushed back Michael (who was a fifth grader and wasn’t usually with Azazel). The others present were shocked at Dean’s sudden outburst and decided to run._

_Dean held a hand out to Castiel. “Are you okay?”_

_Castiel’s big blue eyes were distorted from unleashed tears. He nodded his head and accepted Dean’s hand. “Thank you.”_

_“No problem,” Dean said, flashing his charming smile. “I’m Dean.”_

_“Castiel.”_

_“Well Cas, I’m sorry you had to deal with those guys. But I won’t let them bother you anymore.”_

_And Dean had kept that promise. All through school, they had been inseparable. Azazel and his crew still picked on them but just after their first year of high school, Dean got big. He hit a growth spurt (nothing compared to Sammy) and joined a few sports. Azazel was nothing in comparison and he knew it. With the exception of Michael, who was Castiel’s older brother, they left them alone. In just a few short years, something more began to bloom._

_“Dean…” Cas said softly. He was sitting in the passenger seat of the Impala pretending to watch the movie playing at the drive-in._

_“Yeah, Cas?” Dean looked over with a smile. It fell once he saw the serious look on Cas’ face. “What’s wrong?”_

_“I don’t know if we should be friends anymore.”_

_Dean turned down the connected speakers and turned to face Cas. “Where is this coming from? Is Michael being a dick again?”_

_Cas managed a small laugh. “Always. But he isn’t responsible for this.”_

_“Who is?”_

_“Me, Dean. I just think we’re so different.”_

_Dean stared at Castiel in shock before roaring with laughter. “After ten years of friendship, you just noticed. Don’t bullshit me, Cas. What is this about?”_

_Cas stared hard at the big screen, fighting tears. Dean’s sudden hand on his shoulder didn’t help._

_“Cas. Talk to me… Please.”_

_“I like you, Dean.”_

_Dean smiled. “I like you too, Cas.”_

_Cas shook his head. “No, Dean. I’ve fallen for you.”_

_“I know what you meant.”_

_Cas’ brows furrowed together in confusion. He turned to look at Dean but just as he opened his mouth to speak, Dean’s sweet and full lips were against his. Cas gasped in surprised then reached up and wrapped his arms around Dean’s shoulders. He pulled him close, allowing Dean to devour him._

_Dean tongued Cas’ lips, begging for entrance. When Cas parted them, Dean slipped his tongue inside, gliding against Cas’. “Fuck, I’ve wanted to do this since… forever.”_

_Cas nodded and pulled him back in for another hot and passionate kiss. “I want you, Dean.”_

_Dean pulled back, eyes hooded with lust. He started the car and drove out of the lot like a mad-man. He pulled the car into the gas station and parked behind the building. When he looked at Cas, he stifled a gasp as Cas began to unbutton his shirt. “Are we really about to do this?”_

_Cas looked up, his face full of mock innocence. “Do you not want to?”_

_“I do. I just need to run inside to get a few things.”_

_“I would have thought the great Dean Winchester always came prepared.”_

_Dean shook his head laughing. “Cas. What part of_ I wanted this since forever _, do you not get?”_

_“I don’t understand.”_

_Dean laughed again. “I’ve waited, Cas. Yeah, I’ve made out here and there with some girls, but no farther than that. You’re all I want; all I’ve ever wanted.”_

_Cas smiled brightly and placed a sweet kiss on Dean’s lips. “I love you, Dean Winchester.”_

_“And I love you, Castiel Novak.” Dean kissed him quickly before running into the store. It didn’t take long for him to return with a small bag of essentials. “Condoms and lube. Perfect ingredients for a perfect night.”_

_Cas shook his head laughing. “Are we safe here?”_

_“Oh yeah. Gabe uses it all the time.”_

_“Pig.” Cas cursed his brother._

_“Are you sure about this? Last chance to—”_

_“Dean, would you just shut the fuck up and fuck me already?”_

_He didn’t need to be told twice. Dean climbed into the back with Cas and they quickly undressed each other. Cas was the first to explore the other’s body. He was slow and light with his touches, teasing Dean with his hands and then his mouth. For someone who had never even kissed a person, he sure as hell knew what he was doing. Dean was in ecstasy and was eager to return the favor._

_Cas had to put part of his shirt in his mouth to muffle his screams of pleasure, so they wouldn’t be caught. When Dean had worked him up enough, he entered Cas, joining them at last._

_They stayed connected, not moving for several moments, just to enjoy the feeling of finally being together. When they did move, it was total euphoria and didn’t last too long. Neither were embarrassed by how quick it ended. They were sure they would have many more opportunities to go again._

_They were wrong._

_Two months of a perfect relationship went by in a flash. They were open at their school and were even nominated for Prom Kings. Dean had gotten accepted into his business program and Cas had gotten accepted into a top-notch art school._

_How could he have been so stupid?_

_“You did what?”_

_“I needed the money, Dean. It wasn’t much trouble.”_

_“You’re about to deliver some crazy drugs to Crowley. The King of Shit-storms. He’s going to screw you over.”_

_“I need the money for school, Dean. Michael, Lucifer, and Gabriel got enough scholarships to cover their first year and they worked enough to cover the rest. I don’t have any scholarships, even though I applied to every damn one! And having a decent job while being an art student is damn near impossible.”_

_“Cas, I know about your parents and your own financial problems. My dad has agreed to lend you the money. He said he’ll write up a contract for you and everything and all you have to do, is pay him when you can.”_

_Cas shook his head. “I’m not taking thousands of dollars from my boyfriend.”_

_“It’s a loan. My dad loves you Cas. He’d give you the money if you asked, but he knows you wouldn’t so he said you can pay him back. And how much is Crowley giving you?”_

_“Enough for my first semester.”_

_“And after that? Do you plan to do another dangerous job for him? Don’t think I didn’t see those cuts under your sleeves. You had to fight for whatever is in that bag. I say, throw it away.”_

_“Then Crowley kills me.” Cas said with a sarcastic smile. “Is that what we want?”_

_“Son of a bitch, Cas!” Dean kicked over a nearby stool._

_“I’m leaving now to see him.”_

_“I’m coming with you.” Dean said, firmly._

_“You won’t change my mind.”_

_“Fine.”_

_Cas panicked as he saw the police. Damn Crowley for doing this. “Dean go.” Cas said quickly and pushed Dean further into the dark, so he wouldn’t be seen._

            _“What? No. Come with me.” Dean argued._

 

            _“Crowley must have told them about me. He didn’t know you’d come. Go!” The Cas pushed him and ran out into the open. He got on his knees and held his hands up. Police came and handcuffed his hands together. They pulled him up and led him to the car._

_He just wished he could see Dean again._

“Dean.” Castiel’s voice was gruff and full of surprise. His eyes widened as he looked between him and his brother. “What…”

 

            “Cas… He knows some things.” Gabriel said slowly.

 

            Cas looked away from Dean to glare at his brother. “What did you tell him?”

 

            Cas’ growl actually rose the hairs on Dean’s arms. “Cas.”

 

            He turned his attention back to Dean’s quiet call. Overwhelmed with emotions he left the café.

 

            Dean stood from the booth and ran out after him. “Cas!”

 

            He turned, his eyes glossy with unleashed tears. “I’m sorry. I was expecting this. I don’t know what to say or do.”

 

            “I do.” Dean said and moved to wrap his arms around Cas.

 

            Cas clung to him for dear life, afraid that if he didn’t hold on, he’d lose him again. He fought hard to keep his tears from pouring down.

 

            “We really should talk.”

 

            Cas nodded into Dean’s shoulder and allowed Dean to bring him back inside. They sat down in the booth. Gabriel was back behind the counter.

 

            Cas quickly wiped his eyes and took a deep breath. “It’s been a while since I cried.”

 

            “Yeah. I guess you have an image to maintain, you know, being a crime boss and all.” Dean said, his eyes dark with a mix of anger and confusion.

 

            Cas’ features fell. “Well. I guess I don’t need to go through that then.”

 

            “Oh, you will.” Dean assured. “But first, I want to know what happened after I left.”

 

            Cas thought about it for a moment. “I was brought to jail. It would have just been a local one but since the drugs I delivered were a bit… _extreme_ and turns out they weren’t known to the police, also my involvement with Crowley, I was sent to a high-security prison. Three months had never lasted so long. I had to prove myself quickly so I didn’t become someone’s bitch.”

 

            “What did you do?”

 

            The corners of Cas’ mouth twitched into a shameful smile. “I fought. Hard.”

 

            The thought made Dean nervous. Not for Cas that much, but for the other guys. Cas got tired of being pushed around and so he took up as much fighting classes as he could. Because the guy that ran the gym owed Cas’ father a favor, he let Cas train there for free for the year. Once the guy saw how talented Cas was, he continued to train him for free. Cas became one hell of a fighter.

 

            “What happened after that?”

 

            “I joined a small gang for protection. But they weren’t much help. So I created my own. I gathered the toughest and brightest from others gangs and in a month, I was running the entire prison.”

 

            Dean stifled a gasp. “Did you ever kill anyone?”

 

            Cas bit his lip. “No. But I had people killed for me.”

 

            “Holy fuck.” Dean cursed. “Cas this is crazy! Why did you do that?”

 

            “I had to survive, Dean!” He argued. “If I didn’t establish power and authority, I would have died.”

 

            Maybe Dean could make sense of that. He had seen some prison shows and a high-security prison meant some tough dudes. “So what about when you got out?”

 

            “I wanted to go back to my old life… to you.” Cas looked away as he blushed. He huffed a laugh and continued. “But what happened in prison followed me and I wasn’t able to get away. It was either, confess to crimes I committed in prison and potentially get twenty plus years, join some shit gang like Crowley’s or start my own, like I did in prison.”

 

            “And judging by the massive bank you broke into today, I say you did pretty well, no?”

 

            Cas smiled, his blue eyes gleaming. “I work hard, Dean. I get the plans and blueprints for the banks, I held the police off—”

 

            “How?”

 

            “Oh, I have many connections.” Cas smirked. “And I give them to my men. Everything they grab is all theirs. They split it how they choose and not a cent is mine.”

 

            “Why?”

 

            “When they do good work I reward my employees.” Cas said smoothly.

 

            “Here.” Gabe said, coming up to the table and placing two cups of coffee on the table. “Dean you always drank it black and Cas—”

 

            “Honey and milk.” Dean said for him.

 

            Cas and Gabe stared at Dean in surprise. He nodded to his brother in thanks and leaned forward on the table. “Well… that was interesting.”

 

            Dean bit his lip and cursed internally for the slip. He didn’t know why it came out but it had. “Please continue from before.”

 

            Cas’ grin only widened. “When my employees do good work, I reward them. They have to work for it, yes. But after I’ve set everything up, it’s very easy for them.”

 

            “What about money for yourself?”

 

            “I make millions.”

 

            “What exactly is it you do?”

 

            “Oh, everything really.” Cas said, taking a sip of his coffee. “Not sex trading or human trafficking. I don’t like to put people in danger like that.”

 

            “Drugs aren’t dangerous? Assuming you sell that.”

 

            “I do. And drugs are an easy business. You went to business school, Dean. You should know this.”

 

            “Forgive me, but I think I missed that day when we focused on drug dealing.”

 

            Cas laughed whole-heartedly. He missed Dean’s sense of humor. “Well, it’s mostly dealt to the rich. I make very expensive goods.”

 

            “Okay, so drugs. What else?”

 

            “Weapons to foreign countries.”

 

            “Cas.” Dean gasped in surprise.

 

            “That is actually legal. I deliver it straight to militaries and I have multiple contracts. The only real illegal things are drugs, counterfeit money, smuggling and a few other things that are just as boring.”

 

            “Oh, only that.” Dean shook his head and ran his hands through his hair. “What about Gabe?”

 

            “Oh. Well when I first started really getting into it, I had two other guys help me rob a few banks. Gabe was nearly bankrupt after college so I gave him some money and he created this.” Cas said, lifting his arms to gesture the café. “I told him everything and so he takes part in the robberies when he’s short on cash which isn’t often anymore. He usually just takes it for Mom and Dad.”

 

            “Do they know?”

 

            “Hell no!” Cas said with a laugh. “The only person in my family that knows is Gabe. He’s also the only one that knows my face.” When Dean frowned, Cas continued. “I don’t let any of my employees or people I do business with see my face. It gives me a little more privacy.” He paused to think. “I suppose there are a few handpicked people I trust that have an idea of who I am. But not many.”

 

            “Gabe mentioned a no harm list.”

 

            Cas blushed again. “Ah. Yes… _that._ ”

 

            “Well?”

 

            “I’m one of the top guys in the world. We have a universal code that anyone on our no harm list, cannot be touched. It’s a way to protect our families.”

 

            “What happens if it’s broken?”

 

            “If it was broken by someone who is aware of the list, then they along with their list are killed. No one has ever broken it.”

 

            “And I’m on it?” Dean asked.

 

            Cas nodded. “My family, even _Michael_ ,” Cas said bitterly, “you and your family.”

 

            “My family?”

 

            “I figured if I put your name on the list, if I didn’t put the rest of your family, they could be in danger.”

 

            “Why even put me?”

 

            Cas seemed almost offended by the question. “Because I loved you.”

 

            _And so he kept me on because if he took me off, they’d kill me for shits and giggles no doubt._ “Alright…” Dean said clearing his throat.

 

            “So what now, Winchester? I’ve given you plenty of information to put me away.”

 

            “What makes you think I won’t tell the cops?”

 

            Cas just took a sip of his coffee. He reached into his pocket and pulled out a business card. “Call me if you decide not to get the cops involved.”

 

            “Don’t count on it.”

 

            Cas stood up from the table. “It was good seeing you, Dean. I hope to hear from you soon.” And then he left the café, waving to Gabe as he opened the door.

 

            Dean leaned back in the booth and ran his hands through his hair. How could this be happening? How could Cas have turned out like this?

**Notes for the Chapter:**

> So the next chapter is huge! Almost double this I think but it would be weird to cut it in half.


	5. Poker Night

**Summary for the Chapter:**

> Dean reveals what happened after him after Cas disappeared.  
> Cas gets jealous.

**Notes for the Chapter:**

> It's a little early because I'm busy tomorrow but I hope you enjoy!

 

           It had been two days since Dean had seen Cas. He had been debating contacting the police but every time he picked up the phone, he found himself dialing Cas’ number. He never actually allowed the call to go through, but it was tempting.

 

            He was so conflicted! Cas had pushed Dean to leave back when they were younger and it allowed Dean to live a normal life. Had they both been caught, no doubt Dean would be where Cas is. He wondered how their life would have gone if they had gone to jail together.

 

            There was also the problem about Cas putting him on a no harm list. It wasn’t really a problem, but it showed that he cared. And judging by the longing look on Cas’ when he saw Dean, there was something still there. But could Dean honestly let him get away with this? He stole millions and he’s probably been the cause of many deaths. This was crazy!

 

            He needed more answers.

 

            Dean picked his phone for the tenth time that day and dialed the number. This time, he allowed the call to go through. It rang twice before someone picked up the phone.

 

            “Mr. Emmanuel Allen’s office.” A perky woman spoke.

 

            Um, okay. “Could you let him know Dean Winchester is calling?”

 

            “Yes of course. One moment please.”

 

            Dean held his phone to his ear and began to pace around the island, waiting patiently for the woman to return.

 

            “Dean.” A deep powerful voice said.

 

            The sudden change in tone startled Dean. “Cas…”

 

            “I’m glad you called. I take it this means you didn’t call the police. Or is this a goodbye?”

 

            Dean let out a deep sigh and leaned against the counter. “I feel like even if I did call the police, you’d have a way to save your ass. You were able to hold them off for the rubbery after all.”

 

            Cas chuckled softly. “Yeah. I could. But is that your only reason for not calling them?”

 

            “I would like to talk some more.”

 

            “I would like that as well. Are you at work?”

 

            “No. I’ve taken the rest of the week off. I’ll be back on Monday.”

 

            “I’m leaving for lunch in a little bit. Would you like to join me at Gabe’s?”

 

            “Okay. I’ll be there in about half an hour.”

 

            “See you then.” Cas said fondly.

 

 

            Dean was the first to arrive. He chose a secluded booth in the corner that was away from the other customers. The front door opened and Cas walked in. Dean leaned back, his hands clasped tightly at the sight of him.

 

            It was warmer out so there was no need for the trench coat and suit jacket. Instead, he wore a white long sleeve pinstripe button-down with a black waist coat and dark jeans. He smiled dashingly as he saw Dean. “Nice to see you again.”

 

            “Yeah.” Was all Dean could manage.

 

            “Can I get you, boys, something?” The waitress asked.

 

            “I’ll get my usual.” Cas said smiling, making the girl blush.

 

            “Alright.” She giggled. Seriously. She giggled. “And for you?”

 

            “Burger and fries.”

 

            “And to drink?”

 

            “Water is fine.”

 

            Cas arched an intrigued brow when she walked away. He leaned forward on his elbows and rested his chin in his clasped hands. “No soda?”

 

            “Trying to eat healthier.”

 

            Cas rolled his eyes and laughed. “Sam still on about salads and smoothies?”

 

            “It’s called rabbit food, Cas. And yes. He is.”

 

            “You should listen to him. I noticed you’re a little curvier than before.”

 

            “Hey! I do just fine.”

 

            Cas chuckled again and leaned back with a sigh. “I’ve missed this.”

 

            Dean thought about it. “Me too…”

 

            “Can I ask you something?” Cas asked softly, his blue eyes dim and averting Dean’s intense gaze.

 

            “Yeah.” Dean said tightly, noticing his change in mood.

 

            “You know why I didn’t contact you. I was afraid of getting you involved. But why didn’t you ever try to find me?”

 

            “I did.”

 

            Cas’ eyes met Dean’s and they were full of surprise. “What?” His question was no more than a whisper.

 

            “Gabriel was over in Asia so I couldn’t call him, Lucifer was in college and I didn’t know how to reach him either. I had a feeling you would have been sent to jail but I thought it would be our local one and maybe you’d make bail. When I came home late that night, my parents saw how I looked. I was messy and I couldn’t stop crying. They drilled me for hours and finally, I spilled everything I knew. Dad drove me to school and Mom picked me up. They made sure that besides school, one of them was always with me. They didn’t trust me. After four months of hell, I finally managed to gain their trust back.”

 

            “They didn’t let you leave the house for four months!?”

 

            “I could have gone to jail also, or we could have even been killed. They were furious. Dad was willing to unground me after the first month but Mom got a little…”

 

            “Crazy?” Cas finished for him.

 

            Dean nodded.

 

            “Sounds rights.” Cas never really liked Mary. When Dean had first come out, it was in the tenth grade and Cas had been there. They knew Cas was gay but they didn’t know their son was bisexual. They had expected John to lose his mind over it and Mary calms him down, but the opposite happened. John had risen from the table slowly and pulled his son in for a tight embrace.

 

            Cas remembered seeing the worry vanish from Dean’s face. That was until Mary didn’t move or speak. When Dean tried to talk to her, she began to shout and she even threw a few things around.

 

            John urged Cas to take Dean out of the house so he could cool her down. Dean had been heartbroken. He and John had a rocky relationship and often didn’t see eye to eye on many subjects. But with Mary, well, he had always been her little man. He would never have thought she’d be angry about his sexuality.

 

            It was a few hours later when Cas brought Dean back to his house. He went to say goodbye at the door but instead got an earful from Mary. She blamed Cas for her son’s sexuality and banned Cas from the house. John argued with her, but Mary wasn’t the type of person to lose an argument.

 

            “So… After my Mom found out about what had happened, she blamed everything else on you. _Again_. She called a priest to our house to talk to me about my sexuality.”

 

            “Again?” Cas gasped.

 

            “Yeah. When he got up to my room he stayed for about an hour. We chatted and played a few games of cards. Nice and understanding dude.”

 

            “That’s good.” Cas said, his nerves calming a bit. The first priest had wanted to do an exorcism on Dean because he claimed there was a demon inside him making him desire men. Like what century was this?

 

            “So I went to school and then home for the last two months of school and most of the summer. When I was finally free, I tried to call your house but no one answered. I tried Gabe but his voicemail told me that he was in Asia. I didn’t have Lucifer’s number and so I went to your place. When I got there, Michael answered. I asked where you were and he said you moved with Gabe. He wouldn’t give me your number or anything.” Dean paused as their food came. They thanked the girl then Dean continued. “I was heartbroken, Cas. I knew I couldn’t see you but I thought you’d try to find me. I understand now why you didn’t, but it was the worst feeling in the world.”

 

            Cas heard Dean’s words but then sent him back in time.

 

            _Cas sat in his room, his knees pulled close to his chest. Cas had the room to himself since Gabe was backpacking across Asia for the summer. (He had been saving for almost two years). Not that he really cared about not sharing a room. Gabe had been a good roommate._

_The doorbell rang and Cas made a move to get it._

_“I got it!” Michael called._

_After a few minutes, Cas heard Michael climbing the stairs, heading to his own private never shared room. Cas poked his head out. “Who was that?”_

_“Girl Scouts.” Michael said simply then disappeared into his room._

_Cas went back into his room and sat back on his bed. Adrenaline surged through his body as he thought he heard a familiar roar of an engine but when he looked outside, there was no one._

 

            “I was home.” Cas said quietly as he realized the truth.

 

            “What?”

 

            “Michael answered the door and said it was girl scouts. But I could have sworn I heard the Impala.”

 

            “You were there?” Dean asked, just as surprised.

 

            “I refused to leave my house until I had a plan for my safety.” Cas shook his head in disbelief. “I’m going to kill, Michael.”

 

            “Metaphorically?” Dean asked nervously, chewing on a fry.

 

            Cas chuckled. “I don’t kill people, Dean. But if that bastard would have told me you were there, we could have had a proper goodbye.”

 

            “Why a goodbye?” Dean found himself asking.

 

            Cas frowned a took a few bits of his chicken salad before answering. “I would have told you everything then, Dean. You wouldn’t have wanted a life like that and I wouldn’t want that for you either. It would have been a goodbye.”

 

            “Cas, I loved you. With all my heart. I was ready to have a real life with you, Cas. Do you honestly think I would have pushed you away over some life-saving mistakes? What you did in prison wasn’t cool, but you did it to survive so I can live with it. After that… this is a lot to take in, Cas.”

 

            “I know.” He said. “But I don’t hurt people. I’m getting out of the drug game, smuggling, counterfeit money, even weapons.”

 

            “What would you do?”

 

            “I have enough money saved to retire but I’d open up a few casinos. I have one in Las Vegas that Lucifer runs. He doesn’t know it’s often used as a base, but he’s safe.” Cas ran a hand through his hair out of stress. “I want a semi-normal life. I’m really trying for one. That robbery was our last one. I’ve already shut down two of our factories. I want out, Dean.”

 

            “Okay… Okay.” Dean said trying to wrap his mind around it all. “I want to help.”

 

            “What?” Cas asked, wide-eyed.

 

            “I want to help you in any way I can. Maybe I don’t have the same connections as you, but I’ll help you somehow.”

 

            “Dean, it’s not safe.”

 

            “I don’t care, Cas!” Dean looked around the room and quickly composed himself.

 

            “We haven’t seen each other in fourteen years and when we do, it’s for less than a day. You’re overwhelmed, Dean.” Cas shook his head and went to focus on his meal.

 

            “Cas I’ve always been the guy to do things before thinking, but I’ve rarely had regrets. I know that helping you, will never be a regret.”

 

            “Dean so much has changed.”

 

            “Then let’s be friends again. If I can’t take your lifestyle or you can’t take mine, then I’ll leave if that’s what you want. But I really miss you, Cas. Not a day goes by where I haven’t thought of you.”

 

            Cas’ breath hitched. “Dean, I feel the same.”

 

            “Okay. So it’s a Friday. What are your plans tonight?”

 

            “I was just going to do some finances.”

 

            “Sexy.” Dean said with a roll of his eyes. “The guys and I go to our buddy’s place to play some poker. You should join us.”

 

            “Alright. I haven’t had a guys night out since… well ever.”

 

            Dean chuckled. “Well, I’ll pick you up from work at…?”

 

            “Give me your number and I’ll text it to you.”

 

            Dean gave him his number then immediately received the address to Cas’ work. “So what time should I pick you up?”

 

            “What time do you guys normally meet?”

           

            “Between six and seven.”

 

            “Okay so pick me up at six.” Cas smiled, eager for the time to come.

 

 

            When it did, Dean was waiting in the Impala outside the front doors of a twelve-story building made of shimmering glass. It wasn’t far from Dean’s company.

 

            Cas walked out of the building with a huge smile. He got into the Impala and allowed himself to take it all in. It hadn’t changed. Cassettes were sitting between the driver and passenger seat, the air smelt of leather and it was dust free. Cas dared not look in the back seat. He knew he’d blush at the sight of the spot where they lost their virginity.

 

            “Ready?” Dean asked.

 

            Cas nodded his head. He leaned back in the seat and stifled a laugh as Led Zeppelin began to play. Cas reached for the knob, knowing the outcome.

 

            Dean smacked his hand. “What’s the matter with you!”

 

            Cas roared with laughter.

 

            “You know the rules! Driver picks the music, shotgun shuts his cakehole.”

 

            “I know, I just missed hearing you say it.”

 

            Dean turned his attention to the road, but Cas saw his ears turn red.

 

            “So who’s going to be there?”

 

            “Benny, Sam, maybe Garth but I doubt it, and Kevin.”

 

            “I just know Sam. Unless this Sam isn’t your brother.”

 

            “It is. But he doesn’t know I’ve seen you.”

 

            “You haven’t told him?”

 

            Dean shook his head. “What would I say? Hey Sam? You know Cas, my first love, yeah he’s a major crime boss but he wants out of the business so I’ve decided to help him which is actually a felony but it’s fine.”

 

            Cas nodded. “I like it. I think it’ll work.”

 

            Dean laughed at Cas’ dry tone. He hasn’t felt this light in a long time. Work was always stressful, dating was damn near impossible, and his mother was calling daily to nag him about something new. He dared not get his hopes up about Cas, but he couldn’t deny the amazing feeling of being together again.

 

            They pulled into Benny’s driveway and exited the car. “You’re probably going to lose a lot of money tonight.” Dean said. “Benny has never lost a game of poker.”

 

            “We’ll see…” Cas said with a grin.

 

            Dean led Cas to the garage and went in through the side door. Sam, Benny, and Kevin looked up with smiles but then frowned. Kevin and Benny merely frowned because they didn’t know Cas, but Sam knew. “Dean… What the hell?”

 

            Dean was unsure of Sam’s tone but chose to ignore it. “Guys this is Cas. We grew up together.”

 

            Cas smiled to the group and received a pleasant response, except Sam.

 

            “Dean, a word?”

 

            Dean walked with Sam through the door that led into Benny’s kitchen. “What’s your deal?”

 

            “What the hell is Cas doing here?”

 

            “We caught up.”

 

            “And you’re just fine with how he treated you? Dean, you couldn’t eat and sleep when you found out he had left. You didn’t leave your room for months! You had to start college a year later because you were… you were dead inside Dean!”

 

 

            Cas shifted from foot to foot, gazing at the floor as he heard Dean and Sam’s conversation. The others were in the second part of the garage so they didn’t hear.

 

            “Sam, enough!” Dean had shouted back. “We’ve talked and we’re okay. There are still some issues but we’re working things out. We’re trying to be friends again.”

 

            Cas could hear Sam’s sigh.

 

            When they walked back into the garage, Cas moved closer to the table and pretended he hadn’t heard anything.

 

            “Come have a seat.” Dean said, pulling up a fifth chair.

 

            Cas forced a smile and sat.

 

            “Cas,” Benny said, his southern drawl was thicker due to his beer. “You know how to play Texas Holdem?”

 

            Cas nodded. “I can manage.”

 

            Benny started the game. It went rather fast.

 

            “Fold.” Kevin said.

 

            “Fold.” Sam was next.

 

            “Raise.” Dean threw in his chips.

 

            “All in.” Benny said.

 

            Cas arched a brow at him then glanced at Dean who was the only player left in the current game. “All in.”

 

            “Fold.” Dean said shaking his head.

 

            Benny revealed his cards. “Four of a kind.”

 

            “Oh wow…” Cas nodded his head. “But I’ve got a straight flush.”

 

            Benny’s face fell. “Well damn.”

 

            Dean looked at Cas in surprise but then it dawned on him, Cas owned a casino. No doubt he played all the time.

 

            “How about we try and win my money back?”

 

            Cas nodded his head and began to deal the cards. Sam excused himself to the bathroom and Kevin took a moment to go inside to answer a call from his over worried mother.

 

            “Dean-o, want another beer?” He asked, placing a hand on his shoulder.

 

            “No thanks, Benny. I’m DD.”

 

            Benny grinned. “Don’t want to stay the night again?”

 

            Cas looked up from the deck of cards he had been shuffling and frowned. He began to quietly watch the exchange between Dean and Benny.

 

            “I’ve got to drive Cas home.”

 

            “Well… I have to say I’m a little insulted our Friday night tradition is canceled.” Benny gave Dean’s shoulder a light squeeze.

 

            “Come on, Benny. It’s not like that.”

 

            “So stay tonight. I haven’t had a good lay since last Friday.”

 

            Cas saw red. His hands tightened around the cards to a point where they shot out of his hand. He ignored the strange looks from the other two and picked up the cards.

 

            “Not too good with your hands there?” Benny chuckled darkly.

 

            “Oh, I’m plenty good with my hands.” Cas glared. “And my mouth. Right, Dean? I’m sure you remember after all these years.”

 

            Dean’s eyes widened in surprise at Cas’ words. “Well… I… Um…”

 

            “High school sweethearts right?” Benny arched a brow and leaned forwards on the table. He chewed on a toothpick as he thought. “Does that make you the same Cas that ran out on Dean and broke his heart?”

 

            Cas’ heart dropped. He opened his mouth to speak but Dean spoke first.

 

            “Dude! What the hell was that?”

 

            “Just saying it as it is.”

 

            The conversation died when Sam, followed by Kevin, returned. The game began, followed by a few more. Cas played and won a few more times, but his heart and mind weren’t in it. He kept seeing Benny’s lustful gaze and hearing his harsh words.

 

            “Cas, you okay?” Dean asked as they walked down the driveway.

 

            Cas said nothing as he got into the car. “Just drive me home. I live on West 57th.”

 

            Dean was quiet for a moment. “So do I…” After all this time, they had been so close. “Cas ignore what Benny said. He can be a total asshole and it’s even worse after he’s had a few beers.”

 

            “Are you two dating?”

 

            “No.”

 

            “Just fucking.”

 

            “Cas!” Dean gasped. “What the hell is the matter with you? You don’t get to be jealous after everything that’s happened. It took me years to find someone else. Years! Her and I lasted a bit and then I went to Benny. I’m a handsome, rich thirty-two-year-old and I’ve only been with three people. This isn’t how I thought my life would have gone.”

 

            “What you thought a new babe every night?”

 

            Dean snapped. “No. I thought I’d have a husband to see every day after work and a husband to share a bed with and even start a family. But that didn’t happen so I moved on. Benny and I hook up after poker, but it’s just sex. It’s comfort. He’s tried to get me to go to clubs and meet people there, but I need connection. I need to be with someone I care about.”

 

            “And you care for him.”

 

            “He’s one of my best friends. I sure as hell am not in love with him, but his friendship is comforting.”

 

            Cas sighed, running a hand through his hair. “You’re right. I have no reason to be jealous. It was just surprising.”

 

            “I know, Cas.” Dean said softly, his temper cooling. “But we said friendship.”

 

            “Maybe I want more.” Cas said suddenly. It was a surprise to both of them that those words came out.

 

            “Cas… I need to figure us out first. A lot has changed.”

 

            “I know. I didn’t… No, I did mean it. But I understand and I agree with you. I’m sorry.” He said softly.

 

            Dean wrapped his hand around Cas’. “Don’t be. Truth be told, I want something more too. But it’s going to have to wait. Can you wait for me?”

 

            Cas’ next words were full of truth and pain. “I’d do anything for you.”


	6. Feelings Sting like a Bee

**Summary for the Chapter:**

> Dean and Cas plan a day together, only to get interrupted by Cas' work. Will Dean be able to handle it, or will something new rise?

**Notes for the Chapter:**

> I get kinda a weird vibe about this chapter but at the same time I like it, so I hope you do too.  
> Also, it's a bit shorter than what I'll usually write so expect a range of sizes from chapters.

 

           The drive to Cas’ place was rather quiet and tense. Dean focused on the road ahead, doing his best to ignore the man beside him.

 

            “Right up here,” Cas said, pointing to the large building on the right.

 

            Dean drove around to the back entrance and parked. “Thanks for coming tonight, Cas.” Dean said shyly. “I’m sorry about Benny.”

 

            “I’m glad we were able to do this.” Cas said. He didn’t want to talk about Benny. “Can we do this again?”

 

            “Yeah, for sure. What times work for you?”

 

            “I can make time for you. Is it too soon if I ask to meet tomorrow?”

 

            “No.” Dean shook his head with a smile. “I’ll pick you up at noon?”

 

            “See you then… Unless you want to come up?”

 

            Dean’s breath hitched as he saw Cas’ blue eyes bloom and burst with lust. He really wanted to go. Like _really_ wanted to go. “I can’t. I don’t want to rush anything.”

 

            “I don’t know what you’re talking about.” Cas said with a slight pout and wide eyes to mock innocence. “I just meant for some coffee.”

 

            “Mmhhmm.” Dean said with narrowed eyes. “Of course you did.”

 

            Cas shook his head slowly. “Worth a shot. Text me when you get home.”

 

            “Bye Cas.”

 

            “Goodbye, Dean.”

 

            Dean waved to Cas as he walked through the glass doors. Once Cas was out of sight, Dean drove home. He walked into his living room and threw his jacket over the back of the couch. He pulled out his phone and sent Cas a text.

 

            **I’m home**

**-D**

**Good. Are you going to bed?**

**-C**

**Soon.**

**-D**

Dean was stressed and pent up. He went into his bedroom and undressed and crawled into bed. He opened the drawer in his bedside table and grabbed the lube. He coated his fingers then began to pump himself up. Dean bit his lip as his hand slid up and down his cock. His thumb rubbed the tip, making him groan. He stopped as his phone buzzed.

 

            **What are you doing?**

**-C**

Dean debated answering.

 

            **Just getting ready for his bed.**

**-D**

**I bet you are ;)**

**-C**

**I don’t know what you mean…**

**-D**

**Yes, you do. :P**

**-C**

**I’m going to bed.**

**-D**

**There’s a lot you can do in bed that isn’t sleeping.**

**-C**

**Fine. I’m going to sleep.**

**-D**

**I don’t believe you.**

**-C**

**Believe what you want, but I’m am.**

**-D**

**Goodnight, Dean.**

**-C**

**Night, Cas.**

**-D**

            Dean put his phone down and grabbed some more lube. He coated his hand and began to stroke his cock. He tugged gently, blue eyes flashing behind his eyelids. Dean let out a soft groan as he allowed himself to think of Cas. As his hand tightened on himself, he thought back to one of his favorite nights with Cas.

 

            _He crawled in through Cas’ window and landed on the floor with a thud. Cas sat up quickly in his bed with a gasp._

_“Dean.”_

_“Shh.” He said softly, crawling towards the bed. “Gabe’s staying at his girlfriend’s place so I thought I’d come over. Who else is here?”_

_Cas gulped as Dean got closer to the bed. “Just Mom and Dad but they’re downstairs and at the other end of the house.”_

_“Good.” Dean said and crawled up the bed slowly, much like a panther sneaking up on its prey._

_“Dean.” Cas groaned as Dean’s slips smashed onto his own. Cas brought his hand up and fisted it in Dean’s hair, pulling him closer. Dean pulled the blankets away and was pleased to see that Cas was naked beneath them. He pushed the other down and dragged his nails down his chest until he wrapped his hand around Cas’ member._

_Cas’ hips rolled up in reflex. He moaned into the kiss and rolled his cock into Dean’s hand. He pulled back carefully and grabbed the lube and condoms from the drawer. As he did so, Dean reached down and put Cas in his mouth. “Oh fuck.” Cas groaned and put his hand in Dean’s hair again._

 

_Oh, how Dean loved how submissive and responsive Cas was._

_Dean pushed him down, deep in his throat. He swirled his tongue around his head, making the other gasp. He pulled off with a pop and grinned, pre-come connecting his lips to Cas’ head. He grabbed the lube and coated his fingers and carefully worked Cas open and returned to sucking his cock. He entered one finger in first, carefully pushing it as deep as he could. He added the second and third, moving softly against his prostate._

_“Dean. I need you now.” Cas gasped, thrusting his hips against Dean’s fingers._

_Dean grabbed a condom and covered himself with lube. He sat back on his knees and carefully pushing himself inside Cas. He gasped at how tight Cas was and struggled not to cum. He began to thrust into him._

_“Yes!” Cas gasped, wrapping his legs around Dean’s hips. He gripped Dean’s back and dragged his nails down. “Harder, baby.”_

_Dean lifted Cas a little higher, gripped his hips and pounded into him. “Sweet fuck.”_

_“I’m going to cum!” Cas cried._

_Dean flipped Cas over and pulled him close. He slapped Cas’ cheek, making him gasp with pleasure. He leaned back so his back was to Dean’s front._

_Dean reached to his front and pumped Cas as he thrust into him. “Cum for me.”_

_“Dean!” Cas cried, cumming on his stomach and in Dean’s hand._

Dean gasped Cas’ name as he came over his stomach. When he came down from his high, he blushed as he realized what he had just done. He got up and went into the connecting bathroom and washed. How could he have just done that?! He was trying to start a friendship with Cas, masturbating to him was not helping.

 

            Dean forced the memory out of his head and laid in his bed, praying that when tomorrow came, he wouldn’t look at Cas differently.

 

 

            Cas got into the passenger seat with a smile. Dean returned the smile but his look didn’t linger as memories of last night flooded into his mind. “So um, how about we go for a walk in Central Park?”

 

            “That sounds nice.” Cas said.

 

            Dean drove them to the Park and together they exited the car.

 

            “So… How was your night?” Cas asked with a grin.

 

            “Fine. Yours?”

 

            “It was great.” Cas said, stifling a laugh. “So are we okay, after the Benny incident?”

 

            “I am if you are.”

 

            Cas nodded but before he could speak his phone rang.

 

            Dean frowned as he pulled out two.

 

            Cas groaned as he realized it was his private work phone. “What?” He snapped.

 

            Dean stopped short at Cas’ tone and arched a brow.

 

            “The shipment couldn’t have just disappeared. Who was in charge of it?” Cas waited for a response. “Fuck.” He cursed and ran a hand through his hair. “I’m on my way.” He then turned to Dean. “Sorry, but is there any chance you could drive me to the office? If not, I can call a ride.”

 

            “No, it’s fine.” Dean said and turned, heading back to the car. “What’s going on?”

 

            “A shipment of some pretty heavy narcotics went missing and so did one of the delivery guys.”

 

            “Oh.” Dean didn’t really know how to respond in this situation. There have been issues in the past with his business, but it never involved drugs. “What were they?”

 

            Cas looked at Dean up and down, deciding if he should tell him or not. “It’s called Bumblebee Syndrome, but its street name is BS. It’s a hallucinogen much like LSD but it’s also like cocaine because you get a lot of energy. Bumblebee Syndrome makes you really active and productive. Everyone that’s tried it so far says they’ve completed any and all work they’ve had.” Cas got into the car and let out a sigh. He looked at Dean nervously and asked, “How do you feel about this?”

 

            Dean shrugged. “I mean, it’s going to take a while for you to get out of the game. I’ve been expecting things like this.”

 

            Cas stared at Dean, his eyes narrowed with a mix of worry and confusion. Dean was taking this all too well. He was going to snap and lose it at some point. He just had too.

 

            Dean stopped outside Cas’ building.

 

            Cas opened the door then stopped. “This won’t take too long. I really don’t want to end our day so early so why don’t you come up? I’ll settle everything and then we can go back?”

 

            “Okay.” Dean said with a wide smile. He got out of the car and was stopped by a security guard.

 

            “You can’t park here.”

 

            “It’s fine.” Cas said, stepping out of the car.

 

            The security guard shrank back. “Mr. Allen. My apologies, Sir.”

 

            “It’s alright.” Cas said with a faint grin. “This way, Dean.”

 

            Cas led Dean through the glass doors. The interior of the building was very modern. Everything was either made of white marble or glass. The girl at the front desk looked up with a smile and went to say hi but when she saw that it was Cas, she stopped. She nodded her head curtly and returned to her work.

 

            They climbed into a large elevator. Cas pressed the button for the twelfth floor and leaned against the glass wall. They stopped at a few floors, people moved to enter the elevator but when they saw Cas, they immediately left.

 

            Dean started to notice a pattern.

 

             When the doors opened on the right floor, Cas walked out. Much like downstairs, there was a girl seated behind a desk. Only this one stood up and walked over to Cas. “Mr. Allen, so sorry about the mishap. I have Balthazar waiting in the conference room along with Zachariah and Uriel.”

 

            “Fuck.” Cas cursed for what felt like the twentieth time today. “Thank you, Anna.”

 

            “Of course, Sir.” Her eyes twinkled.

 

            “I’ll wait here.” Dean said, heading towards a sitting area.

 

            “Come in with me. You said you’d leave if you can’t handle my life. I don’t want you to go, but I have to be fair and show you what I do.”

 

            Dean gulped before following Cas into a conference room lined with windows. Two tall men stood talking to each other, both wearing suits and waving their hands around with their angry conversation. The third man was the only one seated and had his legs on the table. He wore a blazer and shirt which would have been appropriate had the shirt not had such a deep V, it would make Simon Cowell and Michelle Visage look twice.

 

            “Ah, Cassie. So nice to see you.” The man that was seated said, his English accent added to his arrogant vibe.

 

            “Balthazar.” Cas said with a nod then turned to the two others. “Zachariah. Uriel. I heard there was an issue.”

 

            “Yeah, there was an issue.” The bald black man said, his voice full of irritation.

 

            “We’ll lose a whole bunch of money if this isn’t found.” The other balding man said, just as annoyed.

 

            “Yes, yes.” Cas said and took a seat.

 

            Dean sat next to him quietly and nervously. He didn’t know what to do right now.

 

            “Who’s this eye-candy?” Balthazar asked, leaning forwards.

 

            “Yes, who is this? Is he going to get the shipment back?” The balding man shrieked.

 

            “Zachariah, please, calm down. Have a seat, both of you.” Though Cas’ voice was calm, it was strong so there was no room for arguments.

 

            The two angry men took a seat at the other end of the table.

 

            “Good.” Cas said with a dark smile that didn’t reach his eyes. “Now, Balthazar, what happened?”

 

            “I don’t really know. One minute, I leave Alfie with the truck to go sign the forms for the delivery and when I come back, he and the entire truck are gone."

 

            “And I’m guessing you had tech turn off the cameras while you dropped off the shipment?”

 

            Balthazar nodded. “Yeah. There’s no footage of anything.”

 

            “Okay…” Cas said running his hands through his hair. “So the shipment arrived, it was just never taken out of the truck.”

 

            “Correct.” Balthazar said.

 

            “Zachariah, call Margo and see what he knows. I’m sure he’s pissed he missed his shipment so be _kind_ and _calm_.”

 

            Zachariah clearly wasn’t impressed by Cas’ condescending tone, but nodded.

 

            “Uriel, contact the factory. I don’t want anything else produced until we find out who stole it and why. I can’t risk losing any more products.”

 

            “And for me boss?” Balthazar leaned towards Cas, his eyes glimmering with mischief. “Perhaps a spanking?”

 

            Uriel and Zachariah groaned and took that as their cue to leave.

 

            “Enough Balthazar.” Cas said firmly. “I want you to call our federal contacts and get an APB out for Alfie.”

 

            Balthazar rolled his eyes. “Alright, fine.” He stood and went to leave the room.

 

            “Come on.” Cas said, leading Dean out as well.

 

            “You going to be okay?” Balthazar asked slowly, wrapping his arm around Cas.

 

            He nodded. “Yeah. It’ll all work out.”

 

            Dean tensed and walked over to Anna who was watching the scene. “Are they…?”

           

            Anna smiled. “No. They dated for three years and were even engaged.”

 

            _What!_ “What happened?”

 

            Anna shrugged and shook her head. “Well, I guess they never were engaged. Balthazar proposed and Cas said no and ended the relationship. It was a surprise to us all. They seemed so happy.”

 

            “Balthazar is really touchy-feely.” Dean said, watching Balthazar cling to Cas.

 

            “He’s like that with everyone. Give him your name and he feels like that’s enough to try and get with you. But I suppose he can be a little extra with Cas.”

 

            “Cas!” Gabriel said walking off the elevator. “Balthazar texted me. What’s going on?”

 

            Cas glared at Balthazar before walking towards his brother. “We lost a shipment. Everything is fine. You can go.”

 

            “Castiel.” Zachariah said, holding his hand over his phone. “I need some help.”

 

            Cas went over to assist.

 

            “Hey, Dean.” Gabriel said.

 

            “Hey, Gabe.”

 

            “So you decided to give Cas a chance?”

 

            “Yeah. I mean he seems he really wants to do better and he did protect me by putting me on that list even though he didn’t have to.”

 

            Gabe grinned. “You still haven’t pieced it together?”

 

            Dean frowned. “What are you talking about?”

 

            “Do you know why Cas put you and your family on that list?”

 

            “Because he loved me. But we had been close.”

 

            “Dean. It took him six years to become such a threat that he earned a _no harm_ list. He didn’t get it right after prison.”

 

            “Holy fuck.” Dean said slowly as he realized the truth.

 

            He didn’t really think about the timeline for everything. He just thought Cas put him on the _no harm_ list. It made sense because he thought that it was after high school, but it was years later. Why would Cas have put him on the _no harm_ list six years later? Cas had told him it was because he loved him, but surely he couldn’t have loved him after six long years.

 

            _Why not? You still love him now._


	7. Mystery Woman

**Summary for the Chapter:**

> Dean and his father get involved in Cas' world.  
> Cas expresses more feelings for Dean.

**Notes for the Chapter:**

> The plot is starting to actually move now :)

 

           Dean tried to keep himself composed. What Gabriel was telling him wasn’t exactly news. It was just Dean didn’t piece it together himself.

 

            Why would Cas even think about him six years later? It was so odd.

 

            “Okay.” Cas said, joining the others. “I think everything is on track to being fixed. There’s no more I can do right now, so how about we get back to it?” He asked Dean but once he saw the look on Dean’s face, he frowned. “What’s wrong?”

 

            “I have so many questions.”

 

            Cas seemed nervous but he nodded his head. “Ask away.”

 

            “It’s not about the shipment from today.” Dean’s words only seemed to confuse Cas more.

 

            “What’s the matter then?”

 

            Dean glanced at Gabe who didn’t seem to care that he had just given Dean some vital information. “Why would you put me on the _no harm_ list—”

 

            “I told you, Dean. I cared for you.”

 

            “No. Why would you put me on the list, _six years later_. This wasn’t just after our separation. It was years later. You still cared about me?”

 

            Cas bit his lip as he felt insulted. “Are you saying that you didn’t care for me anymore at that time?”

 

            “I already told you I’ve never stopped thinking of you. But at the same time, our relationship was around two months. It—”

 

            “It was also ten years of friendship. I’m not just going to ignore that.”

 

            “I know,” Dean said calmly as Cas’ tone became sharper. “But even if you still cared for me, wouldn’t it… I don’t know… _fizzle_ out?”

 

            Cas arched a brow and stood tall. “You were my first and only real friend. To this day, I don’t have a friend like you. I put you on that list because yeah, I cared about you. But I also found out that some of the people your father works with are shady. I’m not saying he takes part because from what I’ve gathered he doesn’t. But that doesn’t change the fact that a lot of people in your field are psychopaths. I did what I could to protect all of you. Is that a better answer?”

 

            “It makes more sense,” Dean said before he could stop himself.

 

            “Oh my God!” Cas cursed throwing his hands in the air. “You Dean Winchester, are the thickest-skulled person I’ve ever met!” Everyone’s eyes were on them now, but they were too heated to noticed. “No matter who it is, you’ve never let yourself be loved. Even when we were together, I’d say I love you, countless times and you’d say it back, and I know you felt it, but you didn’t believe _me_. I tried to prove it to you in any way I could, but you wouldn’t let yourself be loved. Why can’t you just understand that you’re a special person? You’ve done more for me than anyone else so I decided to quietly say thank you. I really didn’t think this was a big deal.”

 

            “Well, it is.”

 

            “I can see that!” Cas laughed out of spite. “But why?”

 

            He didn’t really know why. He supposed he wasn’t angry or annoyed, it was just shocking. “I’m sorry. It’s just surprising.”

 

            Cas seemed to deflate. “Okay… That’s okay. I can understand that.” He said softly and put his hands on Dean’s shoulders. “But I never did any of this to hurt you.”

 

            Dean nodded his head slowly. “Sorry.”

 

            “It’s okay.” Cas took a step back and put his hands on his hips. “We good? You said question _s_.”

 

            Dean looked over Cas’ shoulder to see Zachariah and Uriel pretending to converse but it was clear they were listening. Anna was in paperwork but no doubt she was pretending like the other men. As for Gabe and Balthazar, they were just openly watching.

 

            “Ignore them. What’s up?”

 

            “You and Balthazar—” Balthazar roared with laughter as he knew Dean’s question. “You two were together.”

 

            Cas nodded his head slowly. “Yes. For three years.”

 

            “And he proposed.”

 

            “Yes.”

 

            “You said no.

 

            “Yes.” Cas said, glaring towards, Gabe or Anna knowing it was one of them.

 

            “Why?”

 

            Cas took a deep breath. “Call me crazy… But it turns out I wanted to come home from work to a husband that I love and maybe even have a family with too. When Balthazar proposed, it hit me that if I say yes, no doubt I’d be very happy and get the life I wanted. But, what struck me the most is that I’d never get a second chance at you: the man that worked only a few blocks from my own work and lived only a few houses down from me. It wouldn’t have been fair to start a real life with Balthazar when every day I look over my shoulder hoping to catch a glimpse of you. Maybe I’d see you working on Baby in your driveway, sitting at Cara’s Café down the street or taking a walk with Sam down this very street.”

 

            Dean took a step back to lean against the counter to stabilize himself.

 

            Cas laughed and rubbed the back of his neck nervously. “I know that maybe it sounds stalker-ish. But I couldn’t help but wonder. I think I’d be different if we actually broke-up. But because we were forced apart, I couldn’t let the idea of you, of _us_ go.”

 

            Dean had no words. What does someone even say to that?

 

            “I didn’t mean to spring that all on you. I’m really sorry. I just think if we had a proper goodbye, we could have both moved on and lived our lives. And I always thought that way and so whenever I did see you, because I did… _all the time_ , I thought _what-if_? But then you said that you probably wouldn’t have said goodbye despite everything, so now… I’m going through a lot of emotions.” Cas said honestly.

 

            Still no words.

 

            “Well… This is awkward.” Cas said in a sing-song voice with a clap of his hands.

 

            “Come on.” Dean said. “I want to spend time together.”

 

            Cas let out a breath he didn’t realize he was holding. “Okay. Cool.”

 

            “Hey…” Gabe said slowly, sliding closer to Cas and Dean. “Sorry to interrupt the mood because I along with everyone thoroughly enjoyed that… But can I get a ride.”

 

            Cas looked at Dean and mouthed, _I’m sorry_.

 

            Dean just rolled his eyes. “Yeah, you ass.”

 

            “Great.” Gabe said, already walking towards the elevator.

 

            “I ship it.” Balthazar said as they walked away.

 

            “Fuck off.” They said together.

 

            Dean and Cas sat in the front of the car with Gabe crawling in the back. “Nice ride, Dean. Kept her in good shape.”

 

            “I did. So keep your sticky fingers to yourself and don’t you dare take out that sucker.”

 

            Gabe froze with his hand in his coat pocket, his fingers brushing the sucker. “Noted.”

 

            “Where am I bringing you?”

 

            “My café?”

 

            “Okay. Don’t you have a car?”

 

            “Oh yeah. I just didn’t want to spend money on gas today so I jumped on a bus and now I’m in your car.”

 

            Dean looked to Cas for help but he was just laughing. Before Dean could speak his phone rang. “Cas can you put it on speaker for me?”

 

            “Yeah, it’s Sam.” Cas said.

 

            “Hey, Sammy. What’s up?”

 

            “I know it’s a Saturday but Dad wanted to know if you could look at a new client’s information for Monday.”

 

            “Sure. Why did he call you, though?”

 

            “He wants a lawyer to take a look. Apparently, this woman has a shady past.”

 

            “Okay. I’m heading over to a café called Twig and Berries. Know the place?”

 

            “Um, no. But it sounds like a sex shop.”

 

            “It’s not. I’ll text you the address.”

 

            “Don’t text and drive, idiot!”

 

            Dean groaned. “Cas is with me. He’ll text it.”

 

            “Dean—”

 

            “Kay bye!” Dean said waving for Cas to hang up.

 

            Cas hung up and laughed. “You good?”

 

            “He annoys me sometimes.”

 

           

            They arrived at Gabriel’s café. It was closed this Saturday because Gabe wanted to do inventory, but Gabe opened it up for him. “Thanks for that, Gabe.”

 

            “For sure. I’ll get you guys some coffee.”

 

            Cas and Dean sat at a booth. “Are you okay? I know I dumped a lot on you back there.”

 

            “Yeah. But it was sweet.” Dean said, blushing ever so slightly.

 

            “Glad you don’t think I’m a stalker. Because I’m not… Or am I?” Cas asked, going deep in thought.

 

            Dean reached across the table and took Cas’ hand in his. “Hey, it’s good. We’re good.”

 

            Cas smiled brightly, his cheeks reddening with blush.

 

            Their hands pulled apart as the front door opened with a chime and Sam walked in. “Hey.” He said, glancing at Cas.

 

            “Cas is a business man. He can stay.”

 

            Sam nodded then moved to sit next to Dean. He handed him a file. “Naomi Mitchell. All she needs is a few boats and trains to help move her products which are…” Sam flipped through the file, “statues, paintings, and other antiquities.”

 

            “I think we can fit her in. Her schedule is pretty flexible so we can put her crates on ships and trains that we already have.” Dean said looking through the file.

 

            “Um… Not to interrupt,” Cas spoke softly, “but do you know what she looks like?”

 

            “We don’t have a picture in the file.” Dean said.

 

            “I saw her talking to dad.” Sam said. “She had her hair pulled back, it was dark. She was wearing a grey suit. I got a strange vibe. She smiled and it was nice but also cold. I didn’t like her.”

 

            “Hmm.” Cas leaned back against the booth and shared a look with Dean. “There was a Naomi that was trying to do business with me but she didn’t give me her last name.”

 

            “Why not?” Sam asked with a frown.

 

            “I’m sure she would have, but as soon as I heard _Naomi_ , I hung up. If it’s the same one, she’s absolutely crazy. I know some shady people and even they refuse to do business with her.”

 

            Sam frowned at the information but Dean understood. “What is it that you do?”

 

            “I work in international connections.”

 

            “What is that?”

 

            Cas smiled. “Exactly as it sounds. I help connect people around the world through a mix of methods. That being said, I think you should be careful with her. I don’t know if it’s the same woman or not, but be careful.”

 

            Dean nodded his head. “Copy that.”

 

            “Well, hello.” Gabriel said smoothly, sliding into the booth next to Cas, across from Sam. “Samuel Winchester. You’ve grown up.”

 

            Sam smiled. “Hey, Gabe. How have you been?”

 

            “Better now.”

 

            “Oh, my God.” Dean groaned and looked at Cas who was once again just laughing at Gabriel.

 

            “Does that line actually work?” Sam leaned forward, his lips curled into a grin.

 

            “I don’t know. Do you want to sleep with me yet?”

 

            “No—”

 

            “Yeah, Gabe, enough.” Dean said cutting Sam off.

 

            Gabe glared at Dean then turned back to Sam. “You were saying?”

 

            “I said no.” Dean laughed sarcastically. “Not yet.” Sam added.

 

            “What!”

 

            Gabe’s eyes gleamed with lust towards the younger Winchester.

 

            Cas gapped and shared a look with Dean.

 

            “Sam, stop flirting with Gabe!”

 

            “What’s wrong with flirting?” Sam asked defensively.

 

            “You want to see the kitchen?” Gabe asked, sliding out of the table. “I’ll show you how to… squeeze out some icing from a tight tube.”

 

            “OH MY GAWD!” Dean screamed and threw a nearby menu at Gabe who just laughed. “Cas. Help me out here.”

 

            But Cas had his head in his hands, his shoulders shaking with laughter.

 

            “It’s not funny! That was disgusting.”

 

            “The worst part is Sam got up.” Cas said, tears streaming down his cheeks from laughter.

 

            Dean turned sharply to see that the seat next to him was empty. He looked up to the counter. All he saw was the back of Sam’s body walk through the kitchen door. “Dammit!”

 

            “Dean, as fun as this is, I think we should discuss Naomi. We need to find out if this is, in fact, the same one because if it is, you and your family’s business are in danger.”

 

            “What if we don’t do business with her?”

 

            “She won’t care. She’ll kill you.”

 

            “Whoa. But she didn’t kill you.”

 

            Cas nodded his head slowly, his lips pulled tight. “No offense, but I’m high up in the same world as her. She wouldn’t risk killing me. You guys are well-known business men but are from a different world.”

 

            “I get it.” Dean said honestly. “But we’re on your _no harm_ list. If she kills us, she dies and so does her list.”

 

            “That’s the thing. If this is the same Naomi, she doesn’t have a list.”

 

            “There’s no one she loves?”

 

            Cas shook his head. “She used to be a well-respected business woman, but she got in too deep and went crazy. She killed everyone on her own list so no one could be used against her.”

 

            “Son of a bitch…” Dean gasped. “What about her own life?”

 

            “She’s protected very well. But before we make assumptions, we need to find out if it is her. Then we can figure out a plan.”

 

            “Okay. Should I get Sam?”

 

            Cas thought about it. “I’m sure he’s fine with Gabe. Do you have access to your security cameras? I’d like to see her.”

 

            “I don’t have them, but I know how to get them. We’ll go over to my place. I’m just going to tell Sam we’re going.” Dean got up and went to the kitchen. He walked through the door and groaned. Gabe was sitting on the counter, Sam standing beside him. Gabe was running his hands down Sam’s thick arms and through his hair. “Okay.” Dean said with a roll of his eyes. “Cas and I are going. Have fun, you two.”

 

            “Bye.” They both said, neither looking in his direction.

 

            Dean cursed them then left the café with Cas. “Go through my phone and call Charlie for me.”

 

            “Okay.” Cas said then put it on speaker.

 

            “Sup, lover.”

 

            Dean chuckled. “Hey, kiddo. What are you doing?”

 

            “Just running for a terrible lunch date. Girl was crazy.”

 

            “Which one was it this time?”

 

            “Brooke from HR.”

 

            “What did I say about dating coworkers?” Dean asked sternly, but there was humor in his tone.

 

            “She was in HR! I thought it’d be fine.”

 

            “Whatever. Where are you?”

 

            “Just hoping on the bus. Why?”

 

            “Can you meet me at my place? I’m assuming you have your laptop.”

 

            “Always. Be there in ten.”

 

            “Let yourself in if I’m not there in time.”

 

            “Bye bitch.”

 

            “Bye, Charlie.” Dean said laughing.

 

            “She sounds fun.” Cas said with a smile after hanging up.

 

            “She’s awesome. I met her in college and we immediately clicked. She like the sister I never got.”

 

            Cas liked how fond Dean was of Charlie, especially after clarifying that he thought of her as a sister. It made him immediately like the girl.

 

            They pulled up to Dean’s apartment and headed inside.

 

            Cas was surprised at how rugged the apartment was. They walked into the living room; his couches were worn out leather, light pale green walls with hardwood flooring, a giant flat screen TV was mounted to the wall. The connected kitchen had an island used as a bar and was maybe the most modern part of the apartment with steel appliances and marble counter tops. It was all very _Dean_.

 

            “Hey, Dean.” A fire-haired young woman said walking into sight. She was wearing a worn out black band shirt under a red flannel and ripped jeans. She looked like a Winchester. “Who’s this fine man?”

 

            “This is Cas.”

 

            Charlie’s eyes bulged. “ _The_ Cas. As in Cas from high school. The Cas you loved and loved?”

 

            “Yes yes, Charlie.” Dean said waving his hand.

 

            “It’s so nice to finally meet you!” She squealed and ran forward to give him a hug.

 

            Cas looked at Dean with a frown then accepted the embrace. “Nice to meet you too. You sound very pleasant from what I’ve heard.”

 

            “He’s precious.” Charlie said with a grin to Dean.

 

            “Anyways.” Dean said clearing his throat. “We need to take a look at the security cameras from today.”

 

            “Why?” Charlie asked, moving to the couch and pulling her laptop out of her bag.

 

            “There’s a new potential client if it’s the one that wanted to work with Cas, we should steer clear. Cas needs to see her to tell us if she’s the same one.”

 

            “Okay.” Charlie said, then typed away on her computer. “Where and what time?”

 

            “Dad’s office sometime this morning.”

 

            “Come sit, I’ll fast forward. Tell me when to slow it down.”

 

            Cas and Dean took a seat on either side of Charlie. They watched four small screens, one in John’s office, one pointed at the entrance by the elevator, one at reception and the last in the waiting room. Around ten, the elevator doors opened and a woman in a grey pant suit walked out. Because it was a Saturday, there was no receptionist so John walked out of his office to greet who had entered.

 

            “That’s her. Is there audio?” Castiel asked.           

 

            Charlie shook her head. “No.”

 

            “Well, at least we know.” Dean said and nodded that it was okay to close the cameras. “What should I do, Cas?”

 

            “It’s a tough call. I think you should do business with her.”

 

            “What kind of products does she have?” Charlie asked.

 

            Cas looked at Dean who nodded. “If anyone else should know about the truth Cas, it’s Charlie.”

 

            Cas looked at Charlie again, nervous to trust her but he trusted Dean. “She sells heroin. As bad as heroin is, she somehow made it worse. No one lives to the next day after taking hers.”

 

            “Holy shit.” Charlie gasped.

 

            “Sam said she wanted to transport paintings, sculptures, and antiques, right? Guaranteed it’s hiding in those.”

 

            “Dean, you can’t do business with her.” Charlie stood up.

 

            Dean stood as well and went to grab a beer. “Look, I know it’s risky. But it’s either do business with her or get killed.”

 

            “What!” Charlie shrieked. “She’ll kill you?”

 

            “That’s what she has done in the past to people who say no.”

 

            “She didn’t kill you.” Charlie glared at Cas.

 

            Cas hesitated. “I’m… different. That’s not important right now. What’s important is carefully doing business with her. Act as if she were another client and I can work with my guys to uncover the truth. She’s good at covering her tracks and anyone who has anything on her, well they can’t expose her cause she’ll just expose them.”

 

            “What if your transports get caught?” Charlie asked Dean. “There’s the coast guard, the trains have to stop at boarders, as do trucks.”

 

            “For anyone to see the drugs they’d have to destroy the art pieces.” Cas explained. “Once they’re delivered, Naomi has men to carefully extract the heroin without damaging the art.”

 

            “What about an anonymous tip?” Charlie suggested.

 

            “She’ll have contacts in the police force.” Cas explained. “Even an anonymous tip can be tracked. It’s not hard. The best thing to do is have Dean and his father conduct business with her. I will have some of my men stationed to protect yours. Until we can prove what she’s doing without others getting hurt, we have to go through with the contract.”

 

            “Dean this is crazy.” Charlie said.

 

            Cas didn’t take offense to Charlie’s words. In fact, he was happy she cared for Dean enough to speak her mind and truthfully, it was crazy. But Cas knew this world and he knew that his plan was the best choice.

 

            Dean looked between Charlie and Cas. Charlie’s eyes were wide and pleading. Cas was calm but Dean could see the worry in his features. “Sorry Charlie… I know this is insane, but Cas is right.”

 

            Charlie’s shoulders fell. “Alright. But I’m helping in whatever way I can.”

 

            Dean smiled fondly. “I appreciate that.”

 

            “Good. Now get me a beer, I need a drink.” She said with a groan and threw herself onto the recliner.

 

            Dean laughed and grabbed her one. “Cas?”

           

            “I should call my ride.”

 

            Dean frowned. “Why not stay?”

           

            “It’s getting late.”

 

            Dean’s frown only deepened. He looked outside to see the sun still high in the sky. “It’s not… But you can go if you want. I just would like to finish our day. Even if it’s just sitting inside drinking. I told you, I want to spend time with you.”

 

            Before Cas could speak, Charlie did. “Aren’t you too adorable.”

 

            Cas stared at Dean eyes wide as blush crept into his cheeks. “Dean—”

 

            “Sit and have a beer, Cas. It’ll be fine.”

 

            Famous last words.

 

            Cas sat on the couch, ignoring Charlie’s intrigued glances. She put on a classic episode of Star Trek that was playing and seemed to focus solely on that afterward.

 

            “You okay, Cas?” Dean asked, sitting next to him.

 

            Cas nodded quickly, taking a long swig of beer and watching Kirk kiss another woman that would never appear in the series again.

 

            “Cas.” Dean said softly, placing his hand on Cas’ knee.

 

            Cas stifled a gasp as hot electricity coursed through his body at the touch. “Dean I—”

 

            “I’m leaving.” Charlie said quickly, standing up. “Dorothy just texted me. We’re going to go see a movie.”

 

            “Just kiss her already.” Dean said, watching Charlie grab her coat and laptop bag.

 

            “Back at you.” Charlie said with a grin before leaving the apartment.

 

            “Um…” Cas said awkwardly, cluing into what Charlie had suggested. “Maybe I should go.” He put the beer on the coffee table and made a move to stand.

 

            “Cas, wait!” Dean grabbed his arm and pulled him back down. Cas looked up in surprise.

 

            “Dean…”

 

            “Cas.” Dean said softly, then leaned down and pressed his lips to the other man’s.

 

            Cas gasped at the contact. He reached up and wrapped his arms around Dean’s shoulders. He pulled him close, growling into the kiss. He tongued Dean’s lips, begging for entrance, moaning when he got it. He moved to straddle Dean’s hips, deepening the kiss. “Dean.” He growled, fisting his hands in his hair and shoving his tongue down his throat.

 

            Dean’s head was spinning as Cas dominated the kiss. In the past, he had always been so submissive, and Dean lived for it, but now, he couldn’t imagine it any other way.

 

            Cas rolled his hips against Dean’s creating friction against their hard throbbing cocks.

 

            Dean rolled his head back as Cas rolled his hard beautiful hips against his own. He then gasped as Cas started to kiss down his neck, sucking softly at the salty skin.

 

            Cas pulled back, panting slightly. He gazed into Dean’s eyes intensely. “Dean. What is this?”

 

            “I don’t know, Cas. But I don’t want to stop.”

 

            “Me neither.” Cas said, leaning down and kissing Dean again.

 

            Dean moved to remove Cas’ shirt but then his phone rang. “We need to throw these away.”

 

            “Agreed.” Cas said, continuing to kiss Dean’s neck as he answered the phone.

 

            “Hello?” Dean answered, trying to hide the pleasure in his voice.

 

            “Dean?” Sam asked. “Sorry about the café. I don’t know what came over me. Did you and Cas have a look at the file?”

 

            “Yeah.” Dean said, stifling a moan as Cas bit his ear lobe. “We’re going through with the contract. Everything is fine.”

 

            “Okay. Want me to come by?”

 

            “No!” Dean shouted louder than he meant to. “I mean, no. I’ll see you Monday.”

 

            “Well, dad wants the file so I’m coming over.”

 

            “Dammit, Sammy.” Dean cursed. “Please don’t.”

 

            Sam paused. “Make sure y’all have your clothes on. I’ll be there in ten minutes.”

 

            “If you know we’re hooking up, why are you coming over?” Dean snapped.

 

            Cas pulled back with a frown at Dean’s words.

 

            _Sam_. Dean mouthed.

 

            “I’ll be there soon.” Then Sam hung up.

 

            “He’s on his way to get the file on Naomi. I’m sure dad wouldn’t mind getting it tomorrow or Monday.”

 

            Cas crawled off Dean and back on the couch. “Well, I have to ask. What just happened between us?”

 

            Dean shrugged. “Let’s not put a label on it just yet.” He pulled Cas’ legs over his own and rested his hand on his thigh. “I just want to enjoy our moments.”

 

            Cas nodded his head, his face all smiles.

 

            They kissed each other gently until Sam walked in with Gabriel in tow.

 

            “Well, look at you two!” Gabriel laughed.

 

            Dean pulled back from Cas to glare at the others. “Yes, yes. Here’s the file.” Dean said, leaning forward to grab the file off the coffee table and hand it to Sam. “Okay bye.”

 

            “Dean, can I have a word with you?” Sam said, glancing at Cas who was sitting properly on the couch now.

 

            “If you intend to tell Dean about how I broke his heart back in high school go ahead. I heard you at Benny’s.”

 

            Sam licked his lips nervously. “Okay. Well, it’s true. You left him without a word. We thought he was going to kill himself over you, Cas.”

 

            “Don’t put that on him!” Dean snapped, standing up from the couch to be level with his brother. “Yeah, I was heartbroken but I never thought of suicide. Even if I did, it’s not his fault. Don’t put that kind of weight on him. That’s no fair, Sam. Cas and I talked about how I felt and we’re okay now. There is no need for you to interfere.”

 

            Sam took a step back then looked down at his feet. “I’m sorry, to both of you. I just worry.”

 

            “That’s okay.” Cas said, standing with the others. “I understand your feelings and they’re justified, but I had no choice. There is so much you don’t understand about us but we get each other and I think that’s what matters.”

 

            Sam nodded his head. “Okay… Okay.” Sam turned and headed for the exit. “Gabriel, you coming?”

 

            “I’ll meet you down there.” Once Sam was gone, he continued. “Cas, a word?”

 

            Cas looked at Dean then back to his brother. “Whatever you want to say to me, you can say in front of him.”

 

            “Alright… Cas do you really want to bring Dean into this life?”

 

            “I’m trying to get out of it. He’s helping me.”

 

            “It’s still dangerous.”

 

            “Cas—”

 

            “You don’t get a say, Gabe. This is my choice and if Dean doesn’t want to be a part of it, he will tell me. Now, go.”

 

            Gabe didn’t seem convinced but left the apartment.

 

            “What now?” Dean asked.

 

            Cas looked at him, his gaze full of lust. “I’d really like to fuck you.”

 

            Dean’s breath hitched. “I’d like that.”

 

            “ _But_ , we should take whatever this is, slow.”

 

            “Okay.” Dean said, gulping. “But I’m still going to kiss you.”

 

            Cas grinned. “I’ll let you.”

**Notes for the Chapter:**

> I totally ship Sabriel so I'm probably going to hint at it or maybe just go all out. And if y'all like them, I'll maybe do a short story afterward to express their journey.


	8. Dinner at the Winchesters

**Summary for the Chapter:**

> Cas is invited to dinner at the Winchesters. How will Mary feel having him back?

**Notes for the Chapter:**

> Sorry for the late update!! Life has been very busy so until it dies down I'll only be doing one chapter update a week unless I can catch up. 
> 
> Also this chapter... I don't even know. It feels weird and short but the story will get better once I get over this writer's block.

 

           Monday came around, Dean headed to work, his thoughts of Cas and their hot make-out session. All throughout the morning, he tried to work but his mind’s eye kept filling with deep hypnotizing blue.

 

            “Dean.” Charlie said for what must have been the fifth time.

 

            “What?” He looked up at her.

 

            “You zoned out there, dude.”

 

            “Sorry, Charlie.” Dean said, leaning back in his chair. “Cas and I kissed.”

 

            Charlie’s eyes burst open. “What? Why didn’t you tell me?”

 

            Dean just shrugged. “Because you’ll ask about our relationship but—”

 

            “You don’t know what kind it is.” Charlie finished for him. “That’s okay. But how was it?”

           

            “It was amazing.” Dean said with a wide smile. “I’ve never been breathless after a kiss but with Cas, I can barely speak afterward. I feel like a schoolgirl talking about this.” He said with a shake of his head.

 

            “I like hearing you like this. You were never like this with Lisa and Benny.” Charlie sat across from Dean in one of the two chairs on the other side of his desk. “I’m not trying to put you or whatever it is under pressure, but could you see something coming out of this?”

 

            “I don’t know.” Dean said honestly, leaning forward on his elbows. “I think I want to try something. He said it and I agree, because we were forced apart, and we never got a real goodbye, we were both left wondering. We were each other’s first real friends, first loves, first everything. You don’t forget something like that.”

 

            “So just tell him you still love him!”

 

            Dean licked his lips and shook his head softly. “It’s not that simple. He has a very… troublesome life.”

 

            “He’s involved in drugs isn’t he?”

 

            Dean frowned. “How did—”

 

            “I did some research on him. He works for Allen Corp. I looked into Emmanuel Allen the CEO and there are no pictures of him. I also found that there are a few Emmanuel Allen’s, none of them are the CEO of Allen Corp so I just pieced it together.”

 

            “But how did you know it was drugs?”

 

            “I hacked into their system and found a few of their orders. I’ll give him credit; it’s never taken me so long to break into a place for just a few files.”

 

            “You can’t tell anyone.” Dean said quickly.

 

            “Obviously.”

 

            “Okay, so you get where I’m coming from.”

 

            Charlie nodded. “I’d feel hesitant too, Dean. But there are all kinds of love, each more fucked up than the last.”

 

            “He wants out.”

 

            “That counts for something, no?”

 

            “Yeah. I suppose it does. But I still want to take it slow.”

 

            “Fair.” Charlie said. “So anyways, Naomi is coming in today at ten to meet with you and John.”

 

            “Can’t wait.”

 

           

            Ten o’clock rolled around and Naomi entered the floor with two men in grey suits behind her.

 

            John Winchester met her next to the receptionist and extended his hand. “Nice to see you again, Ms. Mitchell.”

 

            “I’m glad we’ll be doing business together. I was very happy to get your email this morning.”

 

            “Me too.” John said then stepped to the side. “Follow me to our conference room and we’ll finalize the paperwork.”

 

            John, Naomi, and the two other men went into the conference room. The oval table was set up with files at each seat. Dean and Sam both sat at the table, rising when Naomi entered the room.

 

            “Ms. Mitchell, this is my eldest son Dean who I work with. And this is my youngest Sam, who is our company lawyer.”

 

            “Nice to meet you both.” She said with a tight smile, shaking both of their hands.

 

            Dean and Sam returned to their seats, joined by John and Naomi. The two men accompanied with her stood, one behind her and the other by the door. The Winchesters frowned at them but didn’t ask.

 

            “Okay, so we just need to sign a few things and get your schedule.” John explained, gesturing to the file in front of Naomi.

 

            “I’ll have my personal lawyer look these over and I’ll send them back.”

 

            “Of course.” John said.

 

            The rest of the meeting took about an hour to complete. Naomi was now an official client of Winchester Trades. John was under the impression that Naomi had a flexible schedule but it was the opposite. She needed her shipments twice a week on these days at exactly these times. The Winchesters made it work as she was paying them well, but it was strange. Many of the shipments come in around three AM which has happened before due to where the shipments come from and how many rests/gas refills they need. But any shipments that come in between nine PM and six AM are taken to the Winchester Trades warehouse. It holds all the shipments until the clients can send their trucks to pick it up but Naomi needs the shipments brought to her warehouse right away.

 

            “I can’t have them sitting there.” Her voice was calm but her eyes were full of fire. “I will have trucks waiting for the ships at the docks. Your men will not be allowed to touch anything, I will have my employees do all of that.”

 

            John bit back his frowns and protests. “Whatever you need, we will do it.”

 

            “Thank you.” She said, her smile cold and empty of emotions.

 

            “Well, I think that’s everything.” John said, looking to his sons to see if they had anything to add. When they didn’t, John stood. “I’ll walk you out. You have my information so feel free to call me if you need anything. Once I get your papers back, we should be able to pick up your first products this Thursday.”

 

            “Sounds great.”

 

            They walked into the waiting room, all saying their goodbyes.

 

            “Dean.” Charlie said from her desk. “Castiel is here.”

 

            Dean turned and came face-to-face with Cas. “Hey.”

 

            “Hey.” Cas said slowly, glancing towards Naomi. “Sorry, I didn’t know you were in a meeting.”

 

            “It’s fine with me.” Dean said, giving his hand a light squeeze. “I’ll be with you in a second.” Dean moved to join the others but Naomi was right there.

 

            “Castiel. How nice to see you again. It’s been a few years.”

 

            “Yes, it has, Naomi.” Cas said, his lips pulled into a thin tight line.

 

            “It’s a pity you didn’t want to do business with me. But I found the next best thing. The _Winchesters_.”

 

            Both men tensed at her words and shared a look.

 

            “Well, I must be off. Have a nice day.” When she and her goons left, Cas turned to Dean.

 

            “She knows that you and your family are on my list. She’s angry with me for saying no to working with her so she’s going after you.”

 

            “Cas, it will be okay.” Dean said, placing a warm hand on Cas’ shoulder.

 

            “Hey, Castiel!” John called and embraced the boy. “Long time no see.”

 

            Cas smiled brightly at the oldest Winchester. “Mr. Winchester, how are you?”

 

            “I’m good, Cas. How are you? The last I heard of you…” John trailed off glancing nervously at Dean.

 

            “I was in prison.” Cas said with a tight smile. “But it’s all good now.” He didn’t like lying to John Winchester especially after everything he’s done for him. But it was necessary.

 

            “Well, it’s good to see you. Why don’t you come to dinner tonight?”

 

            “Um…” Cas stiffened at the thought. “I don’t want to impose.”

 

            “Nonsense.” John assured. “It would be good to catch up properly.”

 

            “Okay.” Cas said.

 

            “Great. Come over around six?”

 

            “Okay.” He repeated.

 

            John smiled before disappearing into his office.

 

            “Is that okay?” Cas asked.

 

            Dean frowned. “Of course. I think this could be fun.”

 

            “What about your mother?”

 

            Dean shook his head. “Don’t worry about her. I won’t let her hurt you again.”

 

            “Okay…”

 

            “It’ll be okay, Cas.” Sam said, stepping over to join them.

 

            Cas smiled but he was unsure. John had always been welcoming but Mary was another issue.

 

 

            Dean and Cas drove to Mary and John’s house, not far from Dean’s.

 

            “It’s going to be fine.” Dean said once again as they climbed the steps to the front door.

 

            “Just knock.” Cas said, stuffing his hands into the pockets of his trench coat.

 

            Dean knocked and was greeted by Sam. “Just come in, dude.”

 

            Dean shoved at him then smiled at his dad who walked into the foyer. “Hey, Dad.”

 

            “Hey boys.” John gave them both a quick hug. “Your mother is in the kitchen finishing supper.”

 

            “Come on, Cas.” Dean led Cas into the dining room that connected to the open kitchen. “Hey, Mom.” He said, walking over and kissing her on the cheek.

 

            “Hello, sweetie.” She said and turned to put some cut up veggies and cheese on the island for people to snack on. When she laid eyes on Cas, her smile faltered. “Castiel. Long time no see.”

 

            “It’s been a while, Mrs. Winchester.” Cas said, his voice tight.

 

            “Yes, well that’s because you’ve been in prison.”

 

            “Well to be fair, you pushed me away long before that because you believe I turned your son gay.”

 

            “I knew we shouldn’t have invited you.” Mary hissed. “Dean has been so good without you and—”

 

            “Enough, Mary.” John said, entering the room.

 

            “Mom, Cas is a great guy. Please just ease up on him.”

           

            Mary shut her mouth at Dean’s words but her stare was harsh.

 

            “What’s for dinner?” Sam asked.

 

            “Roast and potatoes and cherry pie for dessert.” She said with a grin towards Dean.

 

            “It’s been forever since you’ve made me a pie!”

 

            “Yes well, John said tonight was a special occasion.”

 

            “It is.” John said, clapping Cas on the back. “He’s like a son to me, and now he’s home.”

 

            Cas’ eyes beamed with love towards the elder Winchester. His parents were always so distant and left their children to basically raise themselves. He was thankful to have John back in his life. “Thank you, Sir.”

 

            John gave him a nod then began to set the table.

 

            “I’ve missed this.” Cas said with a sigh.

 

            “Yeah.” Dean agreed. “You always spent your suppers with us. It was quiet without you. But I’m glad you’re back. We’re going to make this all work out.”

 

            “I hope so.”


	9. Limits

**Notes for the Chapter:**

> I'm sorry it's late and short! But bear with me! I'm trying to write ahead but writer's block is a bitch.

 

            “Come on, Cas! Have another slice.”

 

            “No, Dean. If I do, I will die.” Cas’ tone was heavy and serious.

 

            Dean laughed. “Alright, alright.”

 

            “So Cas, we’ve filled you in on our boring new lives moving to New York.” John began. “Tell us about you.”

 

            Cas shrugged. “Not much to tell. I work with international-connections at Allen Corp. And I’ve had a pretty… steady life.” It wasn’t a lie since his life was steadily a disaster.

 

            “Allen Corp eh?” John asked slowly. “I’ve heard there is some shady activity there.”

 

            Dean was surprised at how calm and collected Cas was.

 

            “Well, I suppose. But it pays the bills.”

 

            John nodded his head. “Fair enough. So are you two…”

 

            Dean tensed and glanced at Cas. “We’re just trying to rebuild our friendship.”

 

            “Is it worth that, Dean?” Mary spoke. “He put you through so much.”

 

            “Enough, Mom. I’m a grown man. I can make my own damn choices.” Dean took Cas’ hand in his. “Come on, let’s go upstairs.”

 

            Cas followed Dean up the steps to where his and Sam’s bedroom had been growing up. They passed Sam’s room that still had the keep out sign on the door and went to Dean’s. Dean opened the door slowly and tugged Cas inside. It was still the same as before. The walls were dark blue with classic rock posters pinned to the walls, shelves held comic books and pictures. The bed cover was still of the Scooby Gang with matching pillows.

 

            “You never changed it.” Cas said quietly in awe.

 

            Dean stood behind Cas after closing the door. He put his hands on his sharp hips and rested his chin on his shoulder. “Well, after you left I locked myself in here for… well, I was late to college is all. Then I never came back.”

 

            “I’m sorry—”

 

            “Stop apologizing. I’m okay now. We’re okay now.” Dean placed a sweet kiss to Cas’ exposed neck. “Relax… Think about all the times we spent in here.” Dean dragged his lips up behind Cas’ earlobe. “All those times I pinned you to the bed.” Dean’s hands began to move towards Cas’ middle. “All those times I fucked you so hard, you couldn’t walk.” Dean unbuttoned Cas’ pants and pulled down his fly. “Remember when I made you come so hard, you screamed so loud the neighbors called the police.” Dean’s hand slipping into Cas’ pants, happy to see he wasn’t wearing underwear, he wrapped his hand around Cas’ member.

 

            Cas rolled his head back with a soft moan. “Dean…”

 

            Dean bit Cas’ earlobe gently then began to run his hand up and down Cas’ length. He rubbed his thumb over his head, rubbing the pre-come around his shaft for lube. He tightened his hand, rolling it as he worked Cas up.

 

            Cas groaned as he thrust his hips gently into Dean’s hand. “Dean.” He growled again, moaning as his body rippled with pleasure. Dean’s hand moved at a range of passes, teasing Cas, pushing his limits. “Make me cum.”

 

            “Cum for me, Cas.” Dean quickened his pace, his mouth nipping at Cas’ neck.

 

            “Oh fuck… oh, _Dean_.” Cas gasped, coming hard in Dean’s hand.

 

            “Just like old times.” Dean whispered, placing a kiss to Cas’ cheek.

 

            Cas turned and rested against Dean’s chest. “I haven’t come like that in ages.”

 

            “Glad I could help.” Dean purred, raining kisses on whatever exposed skin he could find.

 

            “I can return—”

 

            “It’s okay, Cas. You don’t have to just yet. I just wanted to touch you again.” Dean kissed him once more then pulled back. “Get cleaned up, we’ll get going.”

 

 

            Cas was thankful to have been invited to the Winchesters, but he didn’t think he could handle Mary again. He had gone through all that in the past and had taken it for Dean. He thought he could do it again, and he could, but he realized that he’s changed. Before he had quietly taken her harsh words, but now he wanted to retaliate but he knew he couldn’t do that.

 

            The dinner with the Winchesters had been last night. Dean had driven him home and left after a hot make-out session in his car. Today, Cas was at his desk, anxiously waiting for noon to arrive. Dean would be coming to his workplace and joining him for lunch.

 

            “Sir.” Anna said, her voice coming in through the phone on his desk. “Zachariah and Uriel have found some information. They’re waiting outside.”

 

            “Send them in.” Cas said the watched as the two of them entered his office and sat at the chairs across from his desk. “Well?”

 

            “We found the missing shipment and Alfie. Everything was still inside.” Zachariah started. “With Alfie, we found Margo. Turns out Margo doesn’t exist. His real name is Dick Roman. He was with Alfie and was brought here. We figured you’d want to talk to him.”

 

            “Yes. Set him up in the room.”

 

            “Already is, Sir.” Uriel said, grinning.

 

            Cas rose from his desk and made his way down the hall. He turned into a room covered in plastic tarps. In the center sat a man in a suit, tied to a chair. His back was to the entrance so he didn’t see Cas. “Dick. Long time no see.”

 

            “Castiel.” Dick purred. “What a pleasure.”

 

            Cas stepped into Dick’s view and crossed his arms over his chest. “I’m going to ask once; why did you take the shipment when I was selling it to you anyways?”

 

            “I got a better offer.”

 

            “From who?”

 

            Dick just grinned.

 

            Cas growled. “From who?”

 

            “Not telling.”

 

            “Then we’re doing this the hard way.”

 

 

            Dean exited the elevator on the top floor and greeted Anna. “Is Cas ready?”

 

            “I saw him leave his office in a hurry but he didn’t say anything. Just wait here and he’ll be back soon.”

 

            “I’m just going to check on him.” Dean said then went into the direction Anna had nodded at. She protested and called him back but Dean didn’t stop. He heard Cas’ voice and headed towards it. He turned and saw Cas through the open doorway. He stood there, his suit ruffled and a mess, his hand full of blood.

 

            “Tell me who the fuck hired you, or I’ll gut you like a fucking fish.” Cas growled, fisting his hand in Dick’s hair.

 

            “No.”

 

            Cas smashed his fist against Dick’s jaw again, the sound of cracking actually echoed. “One more time and then you’re dead.”

 

            “I don’t believe you.”

 

            Cas narrowed his cold eyes before grabbing a knife off of the tray. He held it to Dick’s throat and pressed against it, drawing blood. “ _Who?_ ”

 

            “Naomi.”

 

            Cas growled again then threw the knife away before smashing his fist down again, knocking Dick out cold. “Uriel find Naomi. See why she wants our products.” Cas took his suit jacket and used it to clean his hands. He made a move towards the door then froze as he saw Dean.

 

            Dean stared in horror at Cas. He shook his head and turned sharply, running down the halls to the elevator.

 

            “Dean!”

 

            He didn’t stop.

 

            “Please!” Cas chased Dean down to the ground level and to his car. “Dean, please wait!”

 

            “What the hell, Cas?” Dean shouted, turning so quickly Cas ran into him.

 

            “That’s not me, Dean. That’s who I have to be at work.”

 

            “No, that was fucking insane.”

 

            “Let me just explain myself.” Cas said calmly, placing a hand on Dean’s shoulder.

 

            Dean shoved it off. “No, Cas. I just watched you beat and threaten death on a man. That isn’t normal!”

 

            “None of this is. But I really want to leave the game.”

 

            “Okay, but how am I supposed to react to that? You hurt him good, Cas.”

 

            “He’s a bad man.” Cas tried to defend his actions.

 

            “There are a lot of bad men out there but there are a lot of good men who take them down. You’re not one of them! They’re for the police and F.B.I.”

 

            “I don’t know what to say.” Cas said breathlessly. “I don’t want you to go. How can I fix this?”

 

            Dean shrugged then opened his car door. “Cas this isn’t something you can fix. You’ve been this way for years. I thought you hadn’t changed much but you have. My Cas would have never struck a man that way.”

 

            “Alright. Yes, I’ve changed, but my feelings for you haven’t.”

 

            Dean took a deep breath. “Cas this is over. Whatever this was, it’s over. We were clinging to something that’s long gone.”

 

            “Dean, please. Let’s just go for a drive or sit down somewhere and—”

 

            “And what, Cas? There’s nothing you can say to me that will change my mind.”

 

            _I love you_. But the words wouldn’t come out of Cas’ mouth. “Dean I can’t just stop everything at once. I have to ease my way out carefully otherwise I’ll just get dragged back in and it will all have been for nothing.”

 

            Dean shook his head slowly. “I have to go.” Dean sat in his car and sped out of the lot, leaving Cas standing there, hot tears glistening down his cheeks.

 

            Dean refused to look in his mirrors, he couldn’t see Cas again. He knew if he saw the devastated look on his face he’d turn the car around. He didn’t know where he was driving to but when a familiar café came into view, he pulled in the lot.

 

            Twig and Berries was pretty full as it was lunchtime. Many tables were still empty as most people just lined up for their coffee then left.

 

            Dean saw Gabe standing over a table laughing with customers. When they made eye contact, Dean sat down at a table and pleaded for Gabe to join.

 

            “What’s going on?” Gabe asked, sitting across from Dean.

 

            “Cas and I…” _What? Did we break-up? We weren’t dating._ “I don’t know. We got into a fight.”

 

            “Okay…”

 

            “How do you deal with this Gabe. Despite robbing banks occasionally,” Dean stated sarcastically, “you have a pretty normal life, no?”

 

            “What did you see?”

 

            “I saw him beating a man for answers about something.”

 

            Gabe sucked in his breath and leaned back in his chair. “Fuck…” Then he leaned forward. “He hates it, Dean. He hates everything he does. He’s not like other criminals that thrive off of what they do. What you saw… I can’t excuse it, but also, it’s not really a choice. If Cas were to leave his company suddenly, his title will be stripped and he will have a target on his back along with his list. He has to keep up appearances otherwise, everyone he loves dies.”

 

            “Damn.” Dean cursed and ran a hand through his hair. “Every time he does something stupid or crazy, I forgive him right away. When I found out about this life of his, I barely cared. Even now when I have witnessed what he’s capable of, I don’t care. No, I do care but in a different way. I care about Cas and worry what this is doing to him.” Dean shook his head and looked Gabriel in the eyes. “What I’m feeling isn’t normal. People don’t forgive people like this that easily.”

 

            “They do when they’re in love.” Gabe said softly, all the humor vanishing from his eyes.

 

            “I’m not in love with him.”

 

            “Maybe not _in love_ with him. But you do love him. You always have. You can’t deny that.”

 

            “I don’t want to forgive him.”

 

            “Then don’t.” Gabe said simply. “Take some time to get your thoughts together. What the both of you are doing is tiring and draining. You need to think.”

 

            “I don’t think I can do this, Gabe.”

**Notes for the Chapter:**

> Sorry not sorry for the cliffhanger! :)


	10. The Plan

**Notes for the Chapter:**

> I don't even know how to apologize for the delay. There are so many reasons but I'm just gonna shut up and share with you the last two chapters. Thank you to all those that are still here, I appreciate you so much!
> 
> xoxo

“I’m ready to talk.”

Cas’ breath hitched as he heard Dean’s voice through the phone. “Dean I want—”

“We need to talk in person. Where are you?”

“My place,” Cas said slowly, his throat tightening with nervousness.

“Where is that?”

Cas gave him his address.

“I’ll be there in ten.”

Cas sat down on his leather sofa. His hands clasped together in his lap as he watched the clock tick down. Exactly ten minutes later, there was a knock at the door. Cas got up to answer the door. He wrapped his sweaty hand around the doorknob and opened it. 

Dean stood there, his eyes darker than the night forest. “May I come in?”

“Y-Yes,” Cas said, stepping aside so Dean could walk through the door. “Please have a seat,” Cas said, gesturing to the leather couch across the room.

Dean glanced at the couch then scanned the room. The décor was very modern with steel appliances, black marble countertops, and blue accents. It was very Cas.

Dean reluctantly sat down on the couch.

Cas joined him but kept a cushion between them. “You said you’re ready to talk? I wasn’t expecting—”

“Me to call so soon?” It was true it had only been a few hours.

“No. I wasn’t expecting to hear from you ever again.”

Dean grinned softly before shaking his head. “I don’t think that’s possible. Look, Cas…” He licked his lips. “I know you want out, but it isn’t going to be easy. It will take time. And I feel like I’ve been unfair to you.”

Cas’ brows knit together in that usual way when he was confused. “What do you mean?”

“I feel like I’ve been pressuring you to hurry up and end this life that you’ve started but you can’t do that. And I’ve realized that I need to be more supportive. I don’t like what I saw today… But if this is who you are now… then I’ll just have to love all of you like I used to… “ And you still do, dummy. Dean pushed those thoughts aside for now and focused on the matter at hand.

“So where do we go from here?” Cas asked, his throat tight and his hands pulled at the sleeves of his shirt, from the nerves.

“We keep a strict friendship. No touching, no kissing. Just friends. That’s all I can allow right now.”

“And then what?”

“Cas, I’m not making plans because I don’t think I can rely on you.”

Cas moved back from Dean as if he had been struck. “What?” He asked, his voice soft and full of pain.

Dean shook his head slowly. “That came out harsher than I meant. But I do mean that I don’t know what the future brings. I just know that you’re a part of it so I’m doing what I can.”

Cas nodded slowly. He moved to reach for Dean’s hands but stopped. “I’m sorry.”

“Stop apologizing. I forgive you. Although I don’t think I’m the one you should be apologizing to.”

Cas frowned. “Who?”

“That guy you were beating.”

Cas couldn’t help but let out a bitter laugh. “Dick Roman deserves everything I gave him and more.”

“Okay, so what happens to him?”

“My informant in the F.B.I will take care of him.”

Dean frowned. “Won’t Dick testify against you?”

“They have enough to put him away for life. I made sure of that.”

Dean was shocked at the sudden change in Castiel’s mood. One moment ago he was nervous and fidgeting, much like how he was in high school. Now he was the man that survived prison and built an empire. It’s kinda hot. Dean cursed himself for those thoughts and turned his attention back to the conversation. “Can’t Dick say, hey give me fewer years and I’ll give you a list of names.”

Cas shook his head. “No. He’s already on his way to a maximum security facility.”

“Okay, so that’s one bad guy down. Who next?”

“What?” Cas asked with a frown.

“Well if you want to get out of this life you need to deal with the people who are after you.”

Cas nodded his head slowly. “Alright. That’s true. Dick Roman is gone and all that’s left is Naomi, really. Dick stole a truck of mine even though I was selling to him. He said he got a better offer meaning Naomi may have paid him to steal it so she could use it.”

“What was in the truck? You’re Bumblebee Syndrome or whatever?”

“Yeah.” Cas nodded.

“So she wanted to see your drugs?” Dean asked, confused.

“No. She likely just wanted them destroyed. BS isn’t that terrible of a drug compared to her heroine. People are turning to softer drugs because they’re relaxing or fun. Heroin is just scary so by eliminating my products, there are less on the street and more turf for her.”

“What do we do?”

“I think we should set up a trap,” Cas said, shifting on the couch so his feet were up.

“Isn’t that dangerous?” Dean asked, shifting to face him head-on. “If you want out of this life, you said you had to make it quiet.”

“Naomi is hated by everyone. No one has killed her because she always manages to escape like the snake she is. If we get rid of her, I’ll be able to hand over my companies to Uriel and Zachariah, keep my casinos and live a regular life.”

“What about your list? Your family and mine are on there.”

Cas thought about it for a moment. “I wouldn’t be the first person to leave this life. There have been others that are well respected and because of that, they are allowed to keep their lists posted. I think by taking down Naomi, everyone would be grateful and let me have my list. It sounds strange but we have to risk it. If it doesn’t work, then I’ll continue to sell drugs until we find a new plan.”

“Okay.”

“Okay?!” Cas asked, shocked at the simple word.

“Yes, Cas. Okay. Whatever you need.” Dean said, offering him a sweet smile.

“Dean, I’d like to kiss you again.”

“I know. I’d like to kiss you too. But we can’t.”

Cas let out a low curse that made Dean laugh. “Alright let’s get to it.”

 

The next day, Cas and Dean arrived at Allen Corp. Dean had all of Naomi’s schedules for her shipments and he also knew where her warehouses were. “We can set up F.B.I and S.W.A.T in these areas that will deal with her employees. As for Naomi, she oversees all interactions from a safe place.” Dean said. “I don’t know where that is.”

“I might,” Balthazar said, joining the room. “We grabbed Dick and Alfie not far from a warehouse that isn’t on this list. Perhaps it’s her base.”

“That’s a good place to start. Unfortunately, we can’t go in until the day of, because she’ll know if we’ve been there.”

“Okay, so what do we do?” Dean asked. “Do you want the feds there at that warehouse?”

“No. She’ll see them.” Cas shook his head and took a step back from the table that had a map of the city and files out. “I can get in there.”

“Cas.” Dean said in warning.

“How would you do that?” Balthazar asked.

“She’ll invite me if I reach out to her. I’ll let her know that I know what her plans are. She’ll probably have her goons kidnap me and try to interrogate me.”

“You think she’ll bring you to that warehouse?” Balthazar asked.

Cas shrugged. “If I let her know I know as her shipments are being brought to her, she’ll be forced to bring me there. She has to watch her shipments arrive and so she won’t leave.”

“That’s too dangerous, Cas.”

“It needs to be done, Dean.”

“We’ll have one of our teams near the warehouse where she can’t spot us.” Balthazar explained. “We’ll put a tracker on you so if it doesn’t end up being that warehouse, we can get to you in time.”

“And what good will Cas being there do?” Dean asked, crossing his arms over his chest.

“Dean.” Cas said softly. “I can distract her in time for everyone else to get there.”

“And then she goes to prison. That’s it?” Dean asked. “That might not work.”

“Maybe not. But it’s our only chance.”


	11. The End

The day of Naomi’s shipment arrived. Feds lined the warehouses where the art would be brought and Balthazar and his team awaited outside a warehouse at the other end of the city where they hoped Naomi would be.

Cas picked up his phone and punched in Naomi’s number.

“Cas.”

“Dean. I have to do this.”

Dean bit his lip but took a step back and allowed Cas to do his thing. 

“Naomi.” Cas said, looking to Dean in surprise.

“Castiel. It’s not a good time.”

“Oh no. You’re busy stealing some other shipment of drugs that don’t belong to you?”

“Ah. So Dick cracked.”

Cas rolled his eyes. “Of course he did. And it’s come to my attention that you’ve been a real bitch.”

“Tsk tsk, Castiel. Such language.”

“I want to meet.”

Naomi was quiet on the other end for a minute. “Alright. Meet me two blocks north of your building. You’ll see my boys.”

“I’ll be there in ten minutes.”

“Can’t wait.” Then she hung up.

“Plan is on.” Cas said to Dean, as he grabbed the tracker that would look like an earring.

“Cas I hate this.”

“I know.” He said moving towards the door.

Dean stopped him. “Be careful.”

Cas gave him a nod then left the building and went down to where Naomi said. As he rounded the corner, a van pulled up and he was pulled inside as a sac went over his head.

 

When he was pulled out of the van, he was tied to a chair with his arms behind him. As the bag came off, a hand gripped his throat.

“Hello, Castiel.”

“Naomi.” He hissed.

“Such a pity I’m going to kill you now.”

“You’re a terrible businesswoman.”

Naomi took a step back and crossed his arms over her chest. “Why is that?”

“Because I came here to talk about your business absorbing mine so I could leave this life but you just went straight to violence.”

Naomi’s jaw dropped ever so slightly. “Oh.”

Cas rolled his eyes. His words were a lie but they were believable to her. “What you have done to me isn’t fair but I’ll ignore it.”

“Shh.” She said softly, putting a finger to his lips. “You know what I realized? I could still kill you and take your business. Two birds with one stone.”

“Is that really how you want to conduct business?”

She shrugged. “I think it is. Beat him.”

Fists smashed down onto Castiel. A hand grabbed a handful of his hair and pulled while bringing a fist down across his jaw. He felt his nose shatter and then he felt something sharp in his gut. 

Castiel gasped as he felt the cold knife enter him and his hot blood leave. It was a feeling like no other and it hurt. Bad.

His eyes grew heavy and the lights mixed together, blinding him. He lost consciousness as gunshots rang out.

 

When Castiel awoke, he was in a hospital room. Piles and piles of flowers were on tables and shelves and the TV was on some Spanish channel he couldn’t understand.

“Cas!” Dean called and rushed to his side. “You’re awake!”

“Dean.” Cas said hoarsely. “What happened?”

“Balthazar rushed in, the feds showed up, one of their guys shot Naomi. She’s dead and so is her whole business. Her leading man gave the judge everything they needed to shut it all down. You’re safe and your name is nothing but a victim.”

“Thank fuck.” Cas said, letting himself ease into the mattress.

“They got you good Cas.” Dean took Cas’ hands in his. “I came to the hospital as soon as I heard. You were stabbed and I couldn’t even see your eyes, your face was so swollen. But you look good now. It’s been about a weak.”

“Damn.” Cas moved one of his hands to feel where he had been stabbed. He hissed in pain.

“Dumb ass.” Dean growled.

“I’ve never been stabbed before.”

“Well, it’s gonna be one hell of a scar. Kinda hot too.”

Cas looked to Dean and smiled. “So I’m good. The company will be split between Zach and Uriel.”

“You had the forms already filled out so they signed them. The Casinos are yours.”

“That felt too easy.”

“Cas you were stabbed!” Dean’s hold on Cas’ hands tightened.

“Well, now I can have a normal life.”

“I don’t think normal is your thing.”

 

A week later Cas was healed and released from the hospital. The end of the month was coming and that was when the lists would be updated on the Dark Web. If the list was gone, Cas would have to act fast and contact Zachariah. But if it was there but in gold, it meant Cas was retired and his list was permanent. He didn’t know who made the decisions, he just hoped the answers would be in their favor.

Cas and Dean sat on the couch, watching Cas’ computer. It was the thirty-first of the month at 11:58 p.m. “I’m nervous.” Cas said.

“Me too.” Dean followed. 

As the clock had less than a minute to go, they got close to each other, their hands interlocking and eyes glued to the small screen.

12:00

“Refresh the page.” Dean said.

Cas quickly did so. Then again. And again.

12:01

“What does that mean?”

As Cas opened his mouth, his list moved up the ladder to the top. Its letters were shining gold on the screen.

“Holy fuck.” Cas said.

“Holy fuck.” Dean repeated. They were good. They were going to be fine.

Cas turned around and couldn’t help but move into Dean’s lap and kiss him. Dean wrapped his arms tightly around Cas’ body and held him close. “We’re good.”

Cas nodded quickly then resumed kissing Dean. “I love you.”

Dean groaned in response and pulled back ever so slightly. “I love you too.”

“Make love to me.”

Dean had never moved so quickly in his life. He pulled Cas into his room and tossed him onto the bed, careful of his wounds. He straddled his partner and kissed him again, more intensely than before, if that were possible.

“Dean!” Cas groaned and rolled his hips again the others.

“Gonna make love to you so good, Cas.” Dean purred into his neck.

“No.” Cas said then quickly stood up. Dean looked at him with a confused frown then gasped as Cas pushed him down onto the bed. Cas crawled up to straddle him. He pulled off Dean’s shirt and threw it across the room. He then leaned down and began to suck on one of Dean’s nipples.

Dean gasped softly and put his hand on the back of Cas’ head to urge him on. “Yessss.” Dean hissed as Cas slowly went lower, kissing every inch of exposed skin. Cas undid Dean’s pants and pulled them down, exposing Dean’s nudity.

Cas took Dean’s cock in his hand and slowly pumped it. 

“Fuck.” Dean moaned and thrust his hips up into Cas’ hand.

Cas grinned at the sight of Dean beneath him. He moved lower and spread Dean’s legs and ran his town from his balls down between his cheeks.

Dean gasped again as Cas began to work him open with his tongue. Dean had done plenty things to himself down there but no one had done it to him yet. And the idea of Cas being the first thrilled him. “Fuck me, Cas.”

Cas moved and grabbed lube and condoms from where he knew Dean kept them and slicked his fingers with lube. He slipped a finger inside Dean and began to move it back and forth, brushing softly against his prostate.

“Right there!” Dean begged, thrusting his hips, seeking relief.

“Not yet, baby.” Cas said then quickly undressed and rolled the condom onto his shaft. He slowly entered Dean and hovered over him, allowing them time to both adjust.

“Fuck this is good.” Dean purred. 

Cas was already panting at the sight beneath him. So many times he wanted to pound into Dean, making him cry his name over and over again. He slowly moved his hips, getting a feel for the new environment.

Dean grabbed his hips and urged him on, his eyes shut tight as he bit his lip. “Harder.” He gasped.

Cas grinned then picked up Dean’s legs and wrapped them around his torso. He then thrust himself deep inside Dean, hitting his prostate with every stroke. “I’m gonna cum.” Cas gasped, his hips moving faster and harder.

“Me too.” Dean said, his voice high and tight as pleasure filled him.

Dean and Cas cried out as their bodies erupted. Cas collapsed onto Dean, panting hard. “That was so good.” Cas said.

Dean chuckled softly and ran his fingers through Cas’ hair. “That was amazing.”

Cas looked up at Dean and blushed. “I love you. And I hope we’ll be happy together.”

“I know we will.” Dean said and kissed Cas’ forehead. “Marry me.”  
Cas snapped his head up in shock. “What?”

“Marry me, Castiel.”

“But your mother—”

Dean gave him a look that shut him up fast. “As if that would have anything to do with my happy ending.” Dean carefully rose from the bed, trying to hide the tightness he felt. He moved to his dresser and opened the second drawer. He came back to Cas’ side and kneeled down on the ground. “I got this the moment I turned eighteen.” He held up the little black box and opened it to the black ring that was glittering like stars. “Marry me.”

“Dean.” Cas brought his hands to his mouth in shock as he looked at Dean kneeling on the floor. Not only was he naked, but his soul was laid bare as well. “Yes. I’ll marry you.”

Dean slammed his mouth onto Cas’, slipping the ring on as he did so.

**Notes for the Chapter:**

> Thank you, everyone, for reading this loving yet frustrating story. If I write more I promise to update better!
> 
> Much love,   
> xoxo


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